Enthalpies of Adduct Formation between Boron Trifluoride and Selected Organic Bases in Solution: Toward an Accurate Theoretical Entry to Lewis Basicity
The Lewis basicity of selected organic bases, modeled by the enthalpies of adduct formation between gaseous BF3 and bases in dichloromethane (DCM) solution, is critically examined. Although experimental enthalpies for a large number of molecules have been reported in the literature, it may be desira...
Saved in:
| Published in: | Molecules (Basel, Switzerland) Vol. 26; no. 21; p. 6659 |
|---|---|
| Main Authors: | , , , |
| Format: | Journal Article |
| Language: | English |
| Published: |
Basel
MDPI AG
04-11-2021
MDPI |
| Subjects: | |
| Online Access: | Get full text |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| Abstract | The Lewis basicity of selected organic bases, modeled by the enthalpies of adduct formation between gaseous BF3 and bases in dichloromethane (DCM) solution, is critically examined. Although experimental enthalpies for a large number of molecules have been reported in the literature, it may be desirable to estimate missing or uncertain data for important Lewis bases. We decided to use high-level ab initio procedures, combined with a polarized continuum solvation model, in which the solvated species were the clusters formed by specific hydrogen bonding of DCM with the Lewis base and the Lewis base/BF3 adduct. This mode of interaction with DCM corresponds to a specific solvation model (SSM). The results essentially showed that the enthalpy of BF3 adduct formation in DCM solution was clearly influenced by specific interactions, with DCM acting as hydrogen-bonding donor (HBD) molecule in two ways: base/DCM and adduct/DCM, confirming that specific solvation is an important contribution to experimentally determined Lewis basicity scales. This analysis allowed us to conclude that there are reasons to suspect some gas-phase values to be in error by more than the stated experimental uncertainty. Some experimental values in DCM solution that were uncertain for identified reasons could be complemented by the computed values. |
|---|---|
| AbstractList | The Lewis basicity of selected organic bases, modeled by the enthalpies of adduct formation between gaseous BF3 and bases in dichloromethane (DCM) solution, is critically examined. Although experimental enthalpies for a large number of molecules have been reported in the literature, it may be desirable to estimate missing or uncertain data for important Lewis bases. We decided to use high-level ab initio procedures, combined with a polarized continuum solvation model, in which the solvated species were the clusters formed by specific hydrogen bonding of DCM with the Lewis base and the Lewis base/BF3 adduct. This mode of interaction with DCM corresponds to a specific solvation model (SSM). The results essentially showed that the enthalpy of BF3 adduct formation in DCM solution was clearly influenced by specific interactions, with DCM acting as hydrogen-bonding donor (HBD) molecule in two ways: base/DCM and adduct/DCM, confirming that specific solvation is an important contribution to experimentally determined Lewis basicity scales. This analysis allowed us to conclude that there are reasons to suspect some gas-phase values to be in error by more than the stated experimental uncertainty. Some experimental values in DCM solution that were uncertain for identified reasons could be complemented by the computed values. The Lewis basicity of selected organic bases, modeled by the enthalpies of adduct formation between gaseous BF 3 and bases in dichloromethane (DCM) solution, is critically examined. Although experimental enthalpies for a large number of molecules have been reported in the literature, it may be desirable to estimate missing or uncertain data for important Lewis bases. We decided to use high-level ab initio procedures, combined with a polarized continuum solvation model, in which the solvated species were the clusters formed by specific hydrogen bonding of DCM with the Lewis base and the Lewis base/BF 3 adduct. This mode of interaction with DCM corresponds to a specific solvation model (SSM). The results essentially showed that the enthalpy of BF 3 adduct formation in DCM solution was clearly influenced by specific interactions, with DCM acting as hydrogen-bonding donor (HBD) molecule in two ways: base/DCM and adduct/DCM, confirming that specific solvation is an important contribution to experimentally determined Lewis basicity scales. This analysis allowed us to conclude that there are reasons to suspect some gas-phase values to be in error by more than the stated experimental uncertainty. Some experimental values in DCM solution that were uncertain for identified reasons could be complemented by the computed values. |
| Author | Mó, Otilia Yáñez, Manuel Maria, Pierre-Charles Gal, Jean-François |
| AuthorAffiliation | 1 Institut de Chimie de Nice, UMR 7272, Université Côte d’Azur, Parc Valrose, 06108 Nice, France; Pierre-Charles.MARIA@univ-cotedazur.fr 2 Departamento de Química (Módulo 13, Facultad de Ciencias) and Institute of Advanced Chemical Sciences (IadChem), Campus de Excelencia UAM-CSIC, Cantoblanco, Universidad Autónoma de Madrid, 28049 Madrid, Spain; manuel.yanez@uam.es (M.Y.); otilia.mo@uam.es (O.M.) |
| AuthorAffiliation_xml | – name: 1 Institut de Chimie de Nice, UMR 7272, Université Côte d’Azur, Parc Valrose, 06108 Nice, France; Pierre-Charles.MARIA@univ-cotedazur.fr – name: 2 Departamento de Química (Módulo 13, Facultad de Ciencias) and Institute of Advanced Chemical Sciences (IadChem), Campus de Excelencia UAM-CSIC, Cantoblanco, Universidad Autónoma de Madrid, 28049 Madrid, Spain; manuel.yanez@uam.es (M.Y.); otilia.mo@uam.es (O.M.) |
| Author_xml | – sequence: 1 givenname: Jean-François orcidid: 0000-0002-5500-5461 surname: Gal fullname: Gal, Jean-François – sequence: 2 givenname: Pierre-Charles orcidid: 0000-0001-6089-5860 surname: Maria fullname: Maria, Pierre-Charles – sequence: 3 givenname: Manuel surname: Yáñez fullname: Yáñez, Manuel – sequence: 4 givenname: Otilia orcidid: 0000-0003-2596-5987 surname: Mó fullname: Mó, Otilia |
| BookMark | eNplkk2PEyEYxydmjfuiH8AbiRcvVWAGGDyYdDe7ukmTPWw9EwaeaWkoVGBs-kn8ulK7Ma6eePvl9_yB57I5CzFA07wl-EPbSvxxGz2YyUOmnBLOmXzRXJCO4lmLO3n21_y8ucx5gzElHWGvmvO2E4Jg0V80P29DWWu_c5BRHNHc2skUdBfTVhcXAxqg7AECuo6prpbJjX6KyVlAOlj0CDVAAYse0koHZ9C1zlXkAnqMfjoKPqFl3OtkK47mxkxJF0DLNcQExRntUa2fDqhEtIC9y0eBM64cXjcvR-0zvHkar5pvd7fLm6-zxcOX-5v5YmY6gcusZ5QTQ4HzgcLIBEjTG0qIgN4wrZkkVooe25ESa0ynLR35OPKBSTZ01tr2qrk_eW3UG7VLbqvTQUXt1O-NmFZKp5rUg6LtiDXhVFiiO0poT5lmIAwD2gFwUl2fT67dNGzBGqhX0_6Z9PlJcGu1ij9Uz3pBRFsF758EKX6fIBe1ddmA9zpAnLKiTIpOkrbvK_ruH3QTpxTqUx0pXv-8laJS5ESZFHNOMP4JQ7A6tpD6r4XaX4lVvx8 |
| CitedBy_id | crossref_primary_10_3390_molecules27092900 crossref_primary_10_1039_D3RA02235H crossref_primary_10_1038_s41560_023_01405_6 crossref_primary_10_1016_j_molliq_2022_120997 crossref_primary_10_1002_chem_202302457 crossref_primary_10_1002_jcc_27329 crossref_primary_10_1021_acs_jpcb_2c06315 |
| Cites_doi | 10.1002/jcc.26713 10.1002/wcms.1519 10.1021/ja00895a002 10.1039/D1TA03063A 10.1021/ic50046a017 10.1002/chem.201101071 10.1039/D0TA10366G 10.1080/00304948409356172 10.1021/acs.chemrev.8b00352 10.1016/0040-6031(87)88353-3 10.1021/ed200057b 10.1021/ic50066a002 10.1039/c3ce40285a 10.1021/ja00236a029 10.2174/1573411016999200607171803 10.1021/ja01506a016 10.1021/ic50035a030 10.1063/1.1475333 10.1021/acsenergylett.0c02461 10.1016/j.ccr.2010.04.001 10.1021/acscentsci.0c00334 10.1021/ja01630a069 10.1007/s11224-016-0769-y 10.1016/j.commatsci.2019.109138 10.1007/978-1-4615-8825-2 10.1021/acs.langmuir.9b00262 10.1002/chem.202003916 10.1016/0010-8545(90)85016-L 10.1021/cr9904009 10.1021/jp209200w 10.1021/acs.energyfuels.0c02188 10.1038/s41524-018-0106-7 10.1063/1.2436888 10.1002/adma.202005022 10.1021/jo100461z 10.1021/j100253a048 10.1063/1.5092567 10.1021/cr00088a005 10.1021/acs.jpcc.0c03465 10.1021/ja01506a015 10.1002/9780470681909 10.1016/j.molliq.2020.114506 10.1021/acsenergylett.7b01057 10.1021/ic00063a045 10.1093/oso/9780198551683.001.0001 10.3390/molecules26051411 10.1007/978-3-7091-8194-2 10.1007/BF00650369 10.1007/BF00899944 10.1021/j150545a013 10.1021/jo00101a049 10.1002/cphc.201900691 10.1039/jr9560001248 10.1021/jp501534n 10.1021/ja00814a016 |
| ContentType | Journal Article |
| Copyright | 2021 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License. 2021 by the authors. 2021 |
| Copyright_xml | – notice: 2021 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License. – notice: 2021 by the authors. 2021 |
| DBID | AAYXX CITATION 3V. 7X7 7XB 88E 8FI 8FJ 8FK ABUWG AFKRA AZQEC BENPR CCPQU DWQXO FYUFA GHDGH K9. M0S M1P PIMPY PQEST PQQKQ PQUKI PRINS 7X8 5PM DOA |
| DOI | 10.3390/molecules26216659 |
| DatabaseName | CrossRef ProQuest Central (Corporate) Health & Medical Collection ProQuest Central (purchase pre-March 2016) Medical Database (Alumni Edition) Hospital Premium Collection Hospital Premium Collection (Alumni Edition) ProQuest Central (Alumni) (purchase pre-March 2016) ProQuest Central (Alumni) ProQuest Central UK/Ireland ProQuest Central Essentials ProQuest Central ProQuest One Community College ProQuest Central Korea Health Research Premium Collection Health Research Premium Collection (Alumni) ProQuest Health & Medical Complete (Alumni) Health & Medical Collection (Alumni Edition) Medical Database Publicly Available Content Database ProQuest One Academic Eastern Edition (DO NOT USE) ProQuest One Academic ProQuest One Academic UKI Edition ProQuest Central China MEDLINE - Academic PubMed Central (Full Participant titles) Directory of Open Access Journals |
| DatabaseTitle | CrossRef Publicly Available Content Database ProQuest Central Essentials ProQuest One Academic Eastern Edition ProQuest Health & Medical Complete (Alumni) ProQuest Central (Alumni Edition) ProQuest One Community College ProQuest Hospital Collection Health Research Premium Collection (Alumni) ProQuest Central China ProQuest Hospital Collection (Alumni) ProQuest Central ProQuest Health & Medical Complete Health Research Premium Collection ProQuest Medical Library ProQuest One Academic UKI Edition Health and Medicine Complete (Alumni Edition) ProQuest Central Korea ProQuest One Academic ProQuest Medical Library (Alumni) ProQuest Central (Alumni) MEDLINE - Academic |
| DatabaseTitleList | Publicly Available Content Database CrossRef |
| Database_xml | – sequence: 1 dbid: DOA name: Directory of Open Access Journals url: http://www.doaj.org/ sourceTypes: Open Website |
| DeliveryMethod | fulltext_linktorsrc |
| Discipline | Chemistry |
| EISSN | 1420-3049 |
| ExternalDocumentID | oai_doaj_org_article_23f0a1627d1a4212825a5e7c5e24ee61 10_3390_molecules26216659 |
| GroupedDBID | --- 0R~ 123 2WC 3V. 53G 5VS 7X7 88E 8FE 8FG 8FH 8FI 8FJ A8Z AADQD AAFWJ AAHBH AAYXX ABDBF ABJCF ABUWG ACGFO ACIWK ACPRK AEGXH AENEX AFKRA AFPKN AFRAH AFZYC AIAGR ALIPV ALMA_UNASSIGNED_HOLDINGS BBNVY BENPR BHPHI BPHCQ BVXVI CCPQU CITATION CS3 D1I DIK DU5 E3Z EBD EMOBN ESTFP ESX FYUFA GROUPED_DOAJ GX1 HCIFZ HH5 HMCUK HYE HZ~ I09 IAO ITC KB. KQ8 LK8 M1P M7P MODMG M~E O-U O9- OK1 P2P PDBOC PIMPY PQQKQ PROAC PSQYO RIG RPM SV3 TR2 TUS UKHRP ~8M 7XB 8FK AZQEC DWQXO K9. PQEST PQUKI PRINS 7X8 5PM |
| ID | FETCH-LOGICAL-c470t-85261c2e66b2ef57e9c8c2117e8c5aa591d9780df21dcc4ad2f6ff6b595b4ddd3 |
| IEDL.DBID | RPM |
| ISSN | 1420-3049 |
| IngestDate | Tue Oct 22 15:11:50 EDT 2024 Tue Sep 17 21:14:53 EDT 2024 Fri Oct 25 03:29:48 EDT 2024 Mon Nov 04 11:20:47 EST 2024 Fri Nov 22 02:47:19 EST 2024 |
| IsDoiOpenAccess | true |
| IsOpenAccess | true |
| IsPeerReviewed | true |
| IsScholarly | true |
| Issue | 21 |
| Language | English |
| License | Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
| LinkModel | DirectLink |
| MergedId | FETCHMERGED-LOGICAL-c470t-85261c2e66b2ef57e9c8c2117e8c5aa591d9780df21dcc4ad2f6ff6b595b4ddd3 |
| Notes | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
| ORCID | 0000-0001-6089-5860 0000-0003-2596-5987 0000-0002-5500-5461 |
| OpenAccessLink | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8587173/ |
| PMID | 34771078 |
| PQID | 2596049397 |
| PQPubID | 2032355 |
| ParticipantIDs | doaj_primary_oai_doaj_org_article_23f0a1627d1a4212825a5e7c5e24ee61 pubmedcentral_primary_oai_pubmedcentral_nih_gov_8587173 proquest_miscellaneous_2597491388 proquest_journals_2596049397 crossref_primary_10_3390_molecules26216659 |
| PublicationCentury | 2000 |
| PublicationDate | 20211104 |
| PublicationDateYYYYMMDD | 2021-11-04 |
| PublicationDate_xml | – month: 11 year: 2021 text: 20211104 day: 4 |
| PublicationDecade | 2020 |
| PublicationPlace | Basel |
| PublicationPlace_xml | – name: Basel |
| PublicationTitle | Molecules (Basel, Switzerland) |
| PublicationYear | 2021 |
| Publisher | MDPI AG MDPI |
| Publisher_xml | – name: MDPI AG – name: MDPI |
| References | Smiatek (ref_30) 2021; 322 ref_14 ref_58 ref_12 ref_54 Morris (ref_44) 1966; 5 Chickos (ref_46) 2002; 31 Gupta (ref_24) 2021; 6 Romiluyi (ref_22) 2021; 9 Maria (ref_10) 1987; 109 Kone (ref_8) 2011; 115 Mooibroek (ref_55) 2013; 15 McLaughin (ref_40) 1960; 82 Hamill (ref_17) 2018; 3 Bauer (ref_37) 1956; 76 Bauer (ref_38) 1956; 60 Laurence (ref_6) 2011; 88 Maria (ref_26) 1987; 115 Sacks (ref_41) 1968; 7 Jacquemin (ref_53) 2014; 118 Laurence (ref_7) 2010; 75 Hong (ref_16) 2018; 118 Herbert (ref_60) 2021; 11 Shepp (ref_36) 1954; 76 Gal (ref_35) 2021; 17 Zhang (ref_18) 2019; 35 Allerhand (ref_50) 1963; 85 Smiatek (ref_28) 2019; 150 Jaworski (ref_32) 2016; 27 Morris (ref_43) 1966; 5 Gnida (ref_20) 2020; 34 Rauk (ref_49) 1994; 59 Reed (ref_59) 1988; 88 Mayer (ref_29) 2021; 27 Mills (ref_56) 1984; 16 Clancy (ref_19) 2020; 6 Tomasi (ref_61) 2005; 105 McLaughin (ref_39) 1960; 82 Curtiss (ref_57) 2007; 126 Gal (ref_31) 2019; 20 Pearson (ref_11) 1990; 100 Baek (ref_21) 2020; 32 Hamill (ref_27) 2020; 124 Herbol (ref_34) 2018; 4 Davydova (ref_45) 2010; 254 ref_47 Pomogaeva (ref_62) 2021; 42 Marcus (ref_15) 1984; 13 Drago (ref_52) 1993; 32 Sorenson (ref_33) 2019; 170 ref_42 Drago (ref_51) 1974; 96 Laurence (ref_9) 2011; 17 ref_1 Lee (ref_23) 2021; 9 ref_3 Maria (ref_25) 1985; 89 ref_2 ref_48 ref_5 ref_4 Gutmann (ref_13) 1967; 98 |
| References_xml | – volume: 42 start-page: 1792 year: 2021 ident: ref_62 article-title: Influence of the solvent on the Lewis acidity of antimony pentahalides and group Lewis acids toward acetonitrile and pyridine publication-title: J. Comput. Chem. doi: 10.1002/jcc.26713 contributor: fullname: Pomogaeva – volume: 11 start-page: e1519 year: 2021 ident: ref_60 article-title: Dielectric continuum methods for quantum chemistry publication-title: Wiley Interdiscip. Rev. Comput. Mol. Sci. doi: 10.1002/wcms.1519 contributor: fullname: Herbert – volume: 85 start-page: 1715 year: 1963 ident: ref_50 article-title: A Survey of C-H Groups as Proton Donors in Hydrogen Bonding publication-title: J. Am. Chem. Soc. doi: 10.1021/ja00895a002 contributor: fullname: Allerhand – volume: 9 start-page: 13087 year: 2021 ident: ref_22 article-title: The efficacy of Lewis affinity scale metrics to represent solvent interactions with reagent salts in all-inorganic metal halide perovskite solutions publication-title: J. Mater. Chem. A doi: 10.1039/D1TA03063A contributor: fullname: Romiluyi – volume: 5 start-page: 2156 year: 1966 ident: ref_43 article-title: The addition compounds of some phosphines with boron trifluoride, borane, and trimethylboron publication-title: Inorg. Chem. doi: 10.1021/ic50046a017 contributor: fullname: Morris – volume: 17 start-page: 10431 year: 2011 ident: ref_9 article-title: The Diiodine Basicity Scale: Toward a General Halogen-Bond Basicity Scale publication-title: Chem. Eur. J. doi: 10.1002/chem.201101071 contributor: fullname: Laurence – volume: 9 start-page: 3018 year: 2021 ident: ref_23 article-title: Scalable perovskite coating via anti-solvent-free Lewis acid–base adduct engineering for efficient perovskite solar modules publication-title: J. Mater. Chem. A doi: 10.1039/D0TA10366G contributor: fullname: Lee – volume: 16 start-page: 97 year: 1984 ident: ref_56 article-title: The reactions of amines with methylene chloride. A brief review publication-title: Org. Prep. Proc. Int. doi: 10.1080/00304948409356172 contributor: fullname: Mills – ident: ref_1 – volume: 118 start-page: 10551 year: 2018 ident: ref_16 article-title: Polymerization of Polar Monomers Mediated by Main-Group Lewis Acid—Base Pairs publication-title: Chem. Rev. doi: 10.1021/acs.chemrev.8b00352 contributor: fullname: Hong – volume: 115 start-page: 67 year: 1987 ident: ref_26 article-title: A microcalorimetric method for the measurement of the enthalpies of solution of gases in liquids publication-title: Thermochim. Acta doi: 10.1016/0040-6031(87)88353-3 contributor: fullname: Maria – volume: 88 start-page: 1651 year: 2011 ident: ref_6 article-title: An Overview of Lewis Basicity and Affinity Scales publication-title: J. Chem. Educ. doi: 10.1021/ed200057b contributor: fullname: Laurence – volume: 7 start-page: 1484 year: 1968 ident: ref_41 article-title: Gas-phase enthalpies of adduct formation: Dimethylamine–chloroform and ethyl acetate–boron trifluoride publication-title: Inorg. Chem. doi: 10.1021/ic50066a002 contributor: fullname: Sacks – volume: 15 start-page: 4565 year: 2013 ident: ref_55 article-title: Halogen bonding versus hydrogen bonding: What does the Cambridge Database reveal? publication-title: Cryst. Eng. Comm. doi: 10.1039/c3ce40285a contributor: fullname: Mooibroek – ident: ref_4 – volume: 109 start-page: 483 year: 1987 ident: ref_10 article-title: Chemometrics of the Solvent Basicity: Multivariate Analysis of the Basicity Scales Relevant to Nonprotogenic Solvents publication-title: J. Am. Chem. Soc. doi: 10.1021/ja00236a029 contributor: fullname: Maria – volume: 17 start-page: 328 year: 2021 ident: ref_35 article-title: Can the Lewis Basicity of an Isolated Solvent Molecule be Used for Characterizing Solvent Effects? publication-title: Curr. Anal. Chem. doi: 10.2174/1573411016999200607171803 contributor: fullname: Gal – volume: 82 start-page: 5621 year: 1960 ident: ref_40 article-title: The addition compounds of cyclic ethers with boron trifluoride publication-title: J. Am. Chem. Soc. doi: 10.1021/ja01506a016 contributor: fullname: McLaughin – volume: 5 start-page: 124 year: 1966 ident: ref_44 article-title: The addition compounds of some sulfides with boron trifluoride and with boron trichloride publication-title: Inorg. Chem. doi: 10.1021/ic50035a030 contributor: fullname: Morris – volume: 31 start-page: 537 year: 2002 ident: ref_46 article-title: Enthalpies of sublimation of organic and organometallic compounds. 1910–2001 publication-title: J. Phys. Chem. Ref. Data doi: 10.1063/1.1475333 contributor: fullname: Chickos – ident: ref_48 – volume: 76 start-page: 2061 year: 1956 ident: ref_37 article-title: Energetics of the Boranes. I. The Heats of Reaction of Diborane with the Methylamines, and of Tetramethyldiborane with Trimethylamine; the Dissociation Energy of Diborane publication-title: J. Am. Chem. Soc. contributor: fullname: Bauer – volume: 6 start-page: 224 year: 2021 ident: ref_24 article-title: Evoking High-Donor-Number-Assisted and Organosulfur-Mediated Conversion in Lithium−Sulfur Batteries publication-title: ACS Energy Lett. doi: 10.1021/acsenergylett.0c02461 contributor: fullname: Gupta – volume: 254 start-page: 2031 year: 2010 ident: ref_45 article-title: Molecular complexes formed by halides of group 4,5,13–15 elements and the thermodynamic characteristics of their vaporization and dissociation found by the static tensimetric method publication-title: Coord. Chem. Rev. doi: 10.1016/j.ccr.2010.04.001 contributor: fullname: Davydova – volume: 6 start-page: 464 year: 2020 ident: ref_19 article-title: Balancing Multiple Goals and Making It Work for Materials Research publication-title: ACS Cent. Sci. doi: 10.1021/acscentsci.0c00334 contributor: fullname: Clancy – volume: 76 start-page: 265 year: 1954 ident: ref_36 article-title: Computation of Entropy Increments in Gaseous Bimolecular Associations. I. Donor-Acceptor Reactions publication-title: J. Am. Chem. Soc. doi: 10.1021/ja01630a069 contributor: fullname: Shepp – volume: 27 start-page: 1279 year: 2016 ident: ref_32 article-title: Interactions of polar hydrogen bond donor solvents with ions: A theoretical study publication-title: Struct. Chem. doi: 10.1007/s11224-016-0769-y contributor: fullname: Jaworski – volume: 170 start-page: 109138 year: 2019 ident: ref_33 article-title: How well do implicit solvation models represent intermolecular binding energies in organic-inorganic solutions? publication-title: Comput. Mat. Sci. doi: 10.1016/j.commatsci.2019.109138 contributor: fullname: Sorenson – ident: ref_2 doi: 10.1007/978-1-4615-8825-2 – volume: 35 start-page: 3972 year: 2019 ident: ref_18 article-title: Synergetic Effect of Ethyl Methyl Carbonate and Trimethyl Phosphate on BF4− Intercalation into a Graphite Electrode publication-title: Langmuir doi: 10.1021/acs.langmuir.9b00262 contributor: fullname: Zhang – volume: 27 start-page: 4070 year: 2021 ident: ref_29 article-title: Lewis Acidic Boranes, Lewis Bases, and Equilibrium Constants: A Reliable Scaffold for a Quantitative Lewis Acidity/Basicity Scale publication-title: Chem. Eur. J. doi: 10.1002/chem.202003916 contributor: fullname: Mayer – volume: 100 start-page: 403 year: 1990 ident: ref_11 article-title: Hard and soft acids and bases—The evolution of a chemical concept publication-title: Coord. Chem. Rev. doi: 10.1016/0010-8545(90)85016-L contributor: fullname: Pearson – volume: 105 start-page: 2999 year: 2005 ident: ref_61 article-title: Quantum mechanical continuum solvation models publication-title: Chem. Rev. doi: 10.1021/cr9904009 contributor: fullname: Tomasi – ident: ref_3 – ident: ref_47 – volume: 115 start-page: 13975 year: 2011 ident: ref_8 article-title: Can Quantum-Mechanical Calculations Yield Reasonable Estimates of Hydrogen-Bonding Acceptor Strength? The Case of Hydrogen-Bonded Complexes of Methanol publication-title: J. Phys. Chem. A doi: 10.1021/jp209200w contributor: fullname: Kone – volume: 34 start-page: 14344 year: 2020 ident: ref_20 article-title: Examination of the Effect of Selected Factors on the Photovoltaic Response of Dye-Sensitized Solar Cells publication-title: Energy Fuels doi: 10.1021/acs.energyfuels.0c02188 contributor: fullname: Gnida – volume: 4 start-page: 51 year: 2018 ident: ref_34 article-title: Efficient search of compositional space for hybrid organic–inorganic perovskites via Bayesian optimization publication-title: NPJ Comput. Mat. doi: 10.1038/s41524-018-0106-7 contributor: fullname: Herbol – volume: 126 start-page: 84108 year: 2007 ident: ref_57 article-title: Gaussian-4 theory publication-title: J. Chem. Phys. doi: 10.1063/1.2436888 contributor: fullname: Curtiss – volume: 32 start-page: 2005022 year: 2020 ident: ref_21 article-title: New High Donor Electrolyte for Lithium–Sulfur Batteries publication-title: Adv. Mater. doi: 10.1002/adma.202005022 contributor: fullname: Baek – volume: 75 start-page: 4105 year: 2010 ident: ref_7 article-title: An Enthalpic Scale of Hydrogen-Bond Basicity. 4. Carbon π Bases, Oxygen Bases, and Miscellaneous Second-Row, Third-Row, and Fourth-Row Bases and a Survey of the 4-Fluorophenol Affinity Scale publication-title: J. Org. Chem. doi: 10.1021/jo100461z contributor: fullname: Laurence – volume: 89 start-page: 1296 year: 1985 ident: ref_25 article-title: A Lewis basicity scale for nonprotogenic solvents: Enthalpies of complex formation with boron trifluoride in dichloromethane publication-title: J. Phys. Chem. doi: 10.1021/j100253a048 contributor: fullname: Maria – volume: 150 start-page: 174112 year: 2019 ident: ref_28 article-title: Enthalpic contributions to solvent–solute and solvent–ion interactions: Electronic perturbation as key to the understanding of molecular attraction publication-title: J. Chem. Phys. doi: 10.1063/1.5092567 contributor: fullname: Smiatek – volume: 88 start-page: 899 year: 1988 ident: ref_59 article-title: Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint publication-title: Chem. Rev. doi: 10.1021/cr00088a005 contributor: fullname: Reed – volume: 124 start-page: 14496 year: 2020 ident: ref_27 article-title: Sulfur-Donor Solvents Strongly Coordinate Pb2+ in Hybrid Organic−Inorganic Perovskite Precursor Solutions publication-title: J. Phys. Chem. C doi: 10.1021/acs.jpcc.0c03465 contributor: fullname: Hamill – volume: 82 start-page: 5618 year: 1960 ident: ref_39 article-title: The boron trifluoride addition compounds of dimethyl ether and diethyl ether publication-title: J. Am. Chem. Soc. doi: 10.1021/ja01506a015 contributor: fullname: McLaughin – ident: ref_5 doi: 10.1002/9780470681909 – volume: 322 start-page: 114506 year: 2021 ident: ref_30 article-title: Calculation of donor numbers: Computational estimates for the Lewis basicity of solvents publication-title: J. Mol. Liq. doi: 10.1016/j.molliq.2020.114506 contributor: fullname: Smiatek – ident: ref_12 – volume: 3 start-page: 92 year: 2018 ident: ref_17 article-title: Influence of Solvent Coordination on Hybrid Organic—Inorganic Perovskite Formation publication-title: ACS Energy Lett. doi: 10.1021/acsenergylett.7b01057 contributor: fullname: Hamill – volume: 32 start-page: 2473 year: 1993 ident: ref_52 article-title: Addition of New Donors to the E and C Model publication-title: Inorg. Chem. doi: 10.1021/ic00063a045 contributor: fullname: Drago – ident: ref_58 doi: 10.1093/oso/9780198551683.001.0001 – ident: ref_54 doi: 10.3390/molecules26051411 – ident: ref_14 doi: 10.1007/978-3-7091-8194-2 – volume: 13 start-page: 599 year: 1984 ident: ref_15 article-title: The Effectivity of Solvents as Electron Pair Donors publication-title: J. Solut. Chem. doi: 10.1007/BF00650369 contributor: fullname: Marcus – volume: 98 start-page: 294 year: 1967 ident: ref_13 article-title: Donorstärken in 1,2-Dichloräthan, 3. Mitt. (Donor strengths in 1,2-dichloroethane. Part 3) publication-title: Monatsh. Chem. doi: 10.1007/BF00899944 contributor: fullname: Gutmann – volume: 60 start-page: 1529 year: 1956 ident: ref_38 article-title: Energetics of the Boranes. III. The Enthalpy and Heat Capacity of Trimethylamine-Trifluoroborane as Determined by the Drop Method publication-title: J. Phys. Chem. doi: 10.1021/j150545a013 contributor: fullname: Bauer – volume: 59 start-page: 6808 year: 1994 ident: ref_49 article-title: Lewis acidity and basicity: An ab initio study of proton and BF3 affinities of oxygen-containing organic compound publication-title: J. Org. Chem. doi: 10.1021/jo00101a049 contributor: fullname: Rauk – volume: 20 start-page: 2566 year: 2019 ident: ref_31 article-title: On the Lewis basicity of phosphoramides: A critical examination of their Donor Number through the comparison of enthalpies of adduct formation with SbCl5 and BF3 publication-title: Chem. Phys. Chem. doi: 10.1002/cphc.201900691 contributor: fullname: Gal – ident: ref_42 doi: 10.1039/jr9560001248 – volume: 118 start-page: 4605 year: 2014 ident: ref_53 article-title: Determination of a solvent hydrogen-bond acidity scale by means of the solvatochromism of pyridinium-N-phenolate betaine dye 30 and PCM-TD-DFT calculations publication-title: J. Phys. Chem. B doi: 10.1021/jp501534n contributor: fullname: Jacquemin – volume: 96 start-page: 2082 year: 1974 ident: ref_51 article-title: Solvation Contributions to Enthalpies Measured in Methylene Chloride publication-title: J. Am. Chem. Soc. doi: 10.1021/ja00814a016 contributor: fullname: Drago |
| SSID | ssj0021415 |
| Score | 2.4228766 |
| Snippet | The Lewis basicity of selected organic bases, modeled by the enthalpies of adduct formation between gaseous BF3 and bases in dichloromethane (DCM) solution, is... The Lewis basicity of selected organic bases, modeled by the enthalpies of adduct formation between gaseous BF 3 and bases in dichloromethane (DCM) solution,... |
| SourceID | doaj pubmedcentral proquest crossref |
| SourceType | Open Website Open Access Repository Aggregation Database |
| StartPage | 6659 |
| SubjectTerms | Acids Agreements Approximation Basicity BF3 enthalpies Boron boron trifluoride Chemical bonds Dichloromethane high-level ab initio calculations Hydrogen bonding Lewis base Lewis basicity Solvation Solvents specific solvation |
| SummonAdditionalLinks | – databaseName: Directory of Open Access Journals dbid: DOA link: http://sdu.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwrV1Lb9QwELagF7ggykOkLdUgcUKKGjt-ZLnttrvqAXHpInGL_FQjlaTabMRP4e92nMfSiAOXXmPLcvxNMvPZ428I-Wwpow49QRqCtin6W5-aTOtU8YWhWpqc9vLF1zfq-8_iah1lcg6lvmJO2CAPPCzcBctDpqlkylEdTy-R0WjhlRWece9H4pPJiUyNVIuiXxrOMHMk9Re_hlKzvmWSUSmjMOkjL9SL9c8izHl-5COHs3lNXo2RIiyHGR6TZ75-Q15cTgXa3pI_63p_q-_uketCE2DponQrbKbbiDCmYMEqihTAdleFu67ZVc6Drh3c9AVwvIPhNqaFFfqzFqoapp2yr7Dtc2qxOyyt7aKoBGz_XnyEdSxKAvsGvvnfVRsHqCwG9e_Ij816e3mdjnUWUstVtk8LgTTKMi-lYT4I5Re2sEgMlS-s0FosqIs6RS4grNZy7ViQIUgjFsJw51z-nhzVTe0_EHBGCMdVULwwnBllcsSIZ9Zw7vFnohPyZVr38n6Q0yiRhkSQyn9ASsgqInPoGJWw-wdoH-VoH-X_7CMhZxOu5fh5tiVyPonUCGOxhHw6NCN88bRE177p-j5osDQvioSomT3MJjRvqavbXqK7EEVMbzh5ijc4JS9ZTKSJe9n8jBztd53_SJ63rjvvjf4Bju4MWQ priority: 102 providerName: Directory of Open Access Journals |
| Title | Enthalpies of Adduct Formation between Boron Trifluoride and Selected Organic Bases in Solution: Toward an Accurate Theoretical Entry to Lewis Basicity |
| URI | https://www.proquest.com/docview/2596049397 https://search.proquest.com/docview/2597491388 https://pubmed.ncbi.nlm.nih.gov/PMC8587173 https://doaj.org/article/23f0a1627d1a4212825a5e7c5e24ee61 |
| Volume | 26 |
| hasFullText | 1 |
| inHoldings | 1 |
| isFullTextHit | |
| isPrint | |
| link | http://sdu.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV1Lj9MwELboXuCCeIrAsjISJ6Rsa8ePlFtbWu0BENIWiVvkJxupTaqmET9l_-6OnWTZiBvX2EkszyQzn2fmG4Q-GkKJBUuQeq9MCvbWpXqmVCrZXBMldEYiffHVtfz-K_-yDjQ5fKiFiUn7RpeX1W5_WZU3MbfysDfTIU9s-uPbKud5CB5PJ2gCvuEA0XuURcAkdeHLDPD8dN91mXUNFZQIwQNNaMYkGNbQWe2BLYqU_SM_c5wl-cDsbJ6hp72_iBfdup6jR656gR6vhjZtL9HtujrdqN0BEC-uPV7YQOCKN0NNIu4TsfAyUBXg7bH0u7Y-ltZhVVl8HdvgOIu7mkyDl2DVGlxWeDgv-4y3MbMWpuOFMW2glsDbv-WPeB1ak-BTjb-6P2UTHlAacO1foZ-b9XZ1lfbdFlLD5OyU5hzAlKFOCE2d59LNTW4AHkqXG64UnxMb2IqsB-Eaw5SlXngvNJ9zzay12Wt0VtWVe4Ow1ZxbJr1kuWZUS505J9jMaMYc_FJUgj4N-14cOlKNAsBIkFfxj7wStAySuZ8Y-LDjhfr4u-i1oqCZnykiqLREhRg34F7FnTTcUQbvJgk6H-Ra9B9pUwDyEwCQwCNL0If7YRBfiJmoytVtnANqS7I8T5Ac6cNoQeMR0NtI1N3r6dv_vvMdekJDDk04xmbn6Ox0bN17NGlsexEPDy6i6t8BT3AOqQ |
| link.rule.ids | 230,315,729,782,786,866,887,2106,27933,27934,53800,53802 |
| linkProvider | National Library of Medicine |
| linkToHtml | http://sdu.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV1Lb9NAEF7RcigX3gjTAovECcmNd70Ph1sSEgWRVkgNEjdrn62lxI7iRPyU_l1mHbvU4tard_2QZtaz38433yD02RBKLESC2HtlYoi3LtaJUrFkQ02U0Clp5IvnV_Lyd_ZtGmRyeFcL05D2jS7Oy9X6vCxuGm7lZm0GHU9s8PNikvEsJI8HR-gxrNck6UB6i7MIBKVDAjMFRD9YH_rMupoKSoTgQSg0ZRJCa-itdi8aNaL9vZ1mnyd5L_DMnj3wk5-jp-1OE48Owy_QI1e-RCeTrsHbK3Q7LXc3arUBrIwrj0c2SL_iWVfNiFsKFx4HkQO83BZ-ta-2hXVYlRZfNQ10nMWHak6DxxAPa1yUuDtp-4qXDScXpuORMfsgSoGX_won8TQ0NcG7Ci_cn6IODygMgILX6NdsupzM47ZPQ2yYTHZxxgGGGeqE0NR5Lt3QZAaApXSZ4UrxIbFB58h6cAtjmLLUC--F5kOumbU2fYOOy6p0bxG2mnPLpJcs04xqqVPnBEuMZszBz0hF6Etnr3xzkOPIAcYEO-f_2TlC42DRu4lBSbu5UG2v89Y4OU19ooig0hIVsuOAmBV30nBHGbybROis84e8Xd51DphRALSCvVyEPt0Ng_lCtkWVrto3c8DhSZplEZI9P-p9UH8E3KeR-G7d5d2D7_yITubLi0W--H754xQ9oYGJEw7D2Rk63m337j06qu3-Q7Nw_gJJ1CND |
| linkToPdf | http://sdu.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwpV1Lj9MwELbYRQIuvBGBBYzECSmb2PEj5dZ2Wy1iWa20ReIW-clGapOqacVP4e8yTpOyETe4xpOHNOOMP8_nbxD6YAglFjJB7L0yMeRbF-tUqViykSZK6Iy08sXn1_Lye342CzI5h1ZfLWnf6PK0Wq5Oq_Km5VauVybpeWLJ1ddpzvNQPE7W1idH6C7M2ZT2QL3DWgQS076ImQGqT1b7XrOuoYISIXgQC82YhPQa-qvdykitcP9gtTnkSt5KPvNH__HZj9HDbsWJx3uTJ-iOq56i-9O-0dsz9GtWbW_Ucg2YGdcej22QgMXz_lQj7qhceBLEDvBiU_rlrt6U1mFVWXzdNtJxFu9PdRo8gbzY4LLC_Y7bJ7xoublgjsfG7II4BV78OUCJZ6G5Cd7W-ML9LJvwgNIAOHiOvs1ni-l53PVriA2T6TbOOcAxQ50QmjrPpRuZ3ADAlC43XCk-IjboHVkP4WEMU5Z64b3QfMQ1s9ZmL9BxVVfuJcJWc26Z9JLlmlEtdeacYKnRjDn4KakIfex9Vqz3shwFwJng6-IvX0doErx6MAyK2u2FevOj6BxU0MyniggqLVGhSg7IWXEnDXeUwbtJhE76mCi6ad4UgB0FQCxY00Xo_WEY3BeqLqpy9a61gcAnWZ5HSA5iafBBwxEIoVbquwuZV_985zt07-psXlx8vvzyGj2ggZAT9sTZCTrebnbuDTpq7O5tO3d-Az5gJcM |
| openUrl | ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Enthalpies+of+Adduct+Formation+between+Boron+Trifluoride+and+Selected+Organic+Bases+in+Solution%3A+Toward+an+Accurate+Theoretical+Entry+to+Lewis+Basicity&rft.jtitle=Molecules+%28Basel%2C+Switzerland%29&rft.au=Gal%2C+Jean-Fran%C3%A7ois&rft.au=Maria%2C+Pierre-Charles&rft.au=Y%C3%A1%C3%B1ez%2C+Manuel&rft.au=M%C3%B3%2C+Otilia&rft.date=2021-11-04&rft.eissn=1420-3049&rft.volume=26&rft.issue=21&rft_id=info:doi/10.3390%2Fmolecules26216659&rft.externalDBID=NO_FULL_TEXT |
| thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=1420-3049&client=summon |
| thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=1420-3049&client=summon |
| thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=1420-3049&client=summon |