Unusual resistance of cobalt bis dicarbollide phosphate and phosphorothioate bridged esters towards alkaline hydrolysis: The “metallacarborane effect”
The extraordinary stability of bridged O,O-[cobalt bis(dicarbollide)ion] O-(4-nitrophenyl)phosphorothioate [2]- and phosphate [3]- esters under alkali conditions was discovered. The hydrolysis of metallacarborane esters [2]- and [3]- was studied, and the kinetic and thermodynamic parameters were mea...
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| Published in: | Journal of organometallic chemistry Vol. 896; pp. 70 - 76 |
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| Language: | English |
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15-09-2019
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| Abstract | The extraordinary stability of bridged O,O-[cobalt bis(dicarbollide)ion] O-(4-nitrophenyl)phosphorothioate [2]- and phosphate [3]- esters under alkali conditions was discovered. The hydrolysis of metallacarborane esters [2]- and [3]- was studied, and the kinetic and thermodynamic parameters were measured and compared with those of their organic counterparts, parathion and paraoxon. The extreme differences between the hydrolytic properties of alkyl- and metallacarborane phosphate and phosphorothioate esters are attributed to the electronic and steric effects of the metallacarborane non leaving group (“metallacarborane effect”). The known “thio effect” contributes to a lesser extent to the resistance of [2]- to the basic conditions.
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•Phosphate and phosphorothioate triesters of [Co(1,2-C2B9H11)2]- are resistant to hydrolysis.•High resistance is explained by “metallacarborane effect”, a multifaceted phenomenon.•Metallacarborane produce a charge shielding effect towards approaching nucleophile.•Metallacarborane interact electronically with outer phosphorus bridge.•Steric hindrance and limited flexibility also contribute to the amazing stability. |
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| AbstractList | The extraordinary stability of bridged O,O-[cobalt bis(dicarbollide)ion] O-(4-nitrophenyl)phosphorothioate [2]- and phosphate [3]- esters under alkali conditions was discovered. The hydrolysis of metallacarborane esters [2]- and [3]- was studied, and the kinetic and thermodynamic parameters were measured and compared with those of their organic counterparts, parathion and paraoxon. The extreme differences between the hydrolytic properties of alkyl- and metallacarborane phosphate and phosphorothioate esters are attributed to the electronic and steric effects of the metallacarborane non leaving group (“metallacarborane effect”). The known “thio effect” contributes to a lesser extent to the resistance of [2]- to the basic conditions.
[Display omitted]
•Phosphate and phosphorothioate triesters of [Co(1,2-C2B9H11)2]- are resistant to hydrolysis.•High resistance is explained by “metallacarborane effect”, a multifaceted phenomenon.•Metallacarborane produce a charge shielding effect towards approaching nucleophile.•Metallacarborane interact electronically with outer phosphorus bridge.•Steric hindrance and limited flexibility also contribute to the amazing stability. |
| Author | Leśnikowski, Zbigniew J. Janczak, Sławomir Sardo, Carla |
| Author_xml | – sequence: 1 givenname: Carla surname: Sardo fullname: Sardo, Carla – sequence: 2 givenname: Sławomir surname: Janczak fullname: Janczak, Sławomir – sequence: 3 givenname: Zbigniew J. orcidid: 0000-0003-3158-5796 surname: Leśnikowski fullname: Leśnikowski, Zbigniew J. email: zlesnikowski@cbm.pan.pl |
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| Cites_doi | 10.1021/acs.jmedchem.5b01932 10.1016/S0957-4166(97)00605-8 10.1021/cr050287o 10.1021/ja205850p 10.1016/j.bbapap.2012.04.010 10.1021/ja01086a053 10.1021/jo00102a009 10.1135/cccc19971070 10.1021/jo0511997 10.1135/cccc20020569 10.1016/S0010-8545(00)00262-9 10.1135/cccc19812818 10.1039/C5OB00309A 10.1016/S0022-328X(02)01115-4 10.1135/cccc19970884 10.1055/s-0033-1340847 10.1039/J29700001172 10.1135/cccc19763509 10.1135/cccc19932936 10.1021/ja073652x 10.1007/s00214-018-2272-6 10.1135/cccc19990783 10.1002/chem.201101926 10.1002/chem.200304970 10.1021/jo00921a027 10.1016/S0040-4039(96)02021-7 10.1016/S0022-328X(02)01325-6 10.1039/c2cs15338f |
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| Keywords | Hydrolysis Bridged metallacarborane Phosphorothioate Cobalt bis dicarbollide Phosphate |
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| References | Dash, Satapathy, Swain, Mahanta, Jena, Hosmane (bib5) 2017 (bib7) 2007 Plešek, Císařová, Bačkovský (bib17) 2002; 67 Janoušek, Plešek, Heřmánek, Baše, Todd, Wright (bib22) 1981; 46 Junqueira (bib9) 2018; 137 Plešek, Grüner, Císařová, Báča, Selucký, Rais (bib23) 2002; 657 Purcell, Hengge (bib25) 2005; 70 Farràs, Juárez-Pérez, Lepšík, Luque, Núñez, Teixidor (bib10) 2012; 41 Farràs, Teixidor, Rojo, Kivekäs, Sillanpää, González-Cardoso, Viñas (bib29) 2011; 133 Kirby, Medeiros, Oliveira, Orth, Brandão, Wanderlind, Amer, Williams, Nome (bib34) 2011; 17 DuBay, Grieco, Todd (bib14) 1994; 59 Plešek, Grüner, Báča, Fusek, Císařová (bib36) 2002; 649 Grüner, Cisařová, Franken, Plešek (bib20) 1998; 9 Plesek, Hermanek, Base, Todd, Wright (bib19) 1976; 41 (bib1) 2018; vol. 865 Ora, Lönnberg, Lönnberg (bib27) 2012 Ruben, Plumley, Chapman, Evanseck (bib28) 2008; 130 Hosmane, Eagling (bib3) 2018 Grüner, Rais, Selucký, Bubeníková (bib12) 2012 Khan, Kirby (bib31) 1970; 0 Rojo, Teixidor, Viñas, Kivekäs, Sillanpää (bib30) 2003; 9 (bib2) 2015; vol. 798 Grieco, DuBay, Todd (bib15) 1996; 37 Hawthorne, Young, Wegner (bib8) 1965; 87 Leśnikowski (bib13) 2016; 59 Sivaev, Bregadze (bib6) 2002; 64 Kirby, Mora, Nome (bib35) 2013; 1834 Plesek, Gruner, Holub (bib18) 1997; 62 Akiyama, Saito, Janczak, Lesnikowski (bib16) 2014; 25 Plešek, Grüner, Fusek, Votavová (bib24) 1993; 58 Romanovskiy, Smirnov, Babain, Yu Shadrin (bib11) 2011 Grimes (bib4) 2000; 200–202 Cleland, Hengge (bib33) 2006; 106 Franken, Plešek, Fusek, Semrau (bib21) 1997; 62 Wadsworth, Tsay (bib32) 1974; 39 Carvalho, O'Donoghue, Hodgson, Kamerlin (bib26) 2015; 13 Ora (10.1016/j.jorganchem.2019.06.001_bib27) 2012 Farràs (10.1016/j.jorganchem.2019.06.001_bib29) 2011; 133 Cleland (10.1016/j.jorganchem.2019.06.001_bib33) 2006; 106 Plešek (10.1016/j.jorganchem.2019.06.001_bib24) 1993; 58 Plešek (10.1016/j.jorganchem.2019.06.001_bib36) 2002; 649 Grimes (10.1016/j.jorganchem.2019.06.001_bib4) 2000; 200–202 Romanovskiy (10.1016/j.jorganchem.2019.06.001_bib11) 2011 Khan (10.1016/j.jorganchem.2019.06.001_bib31) 1970; 0 Sivaev (10.1016/j.jorganchem.2019.06.001_bib6) 2002; 64 Grieco (10.1016/j.jorganchem.2019.06.001_bib15) 1996; 37 Purcell (10.1016/j.jorganchem.2019.06.001_bib25) 2005; 70 (10.1016/j.jorganchem.2019.06.001_bib7) 2007 Junqueira (10.1016/j.jorganchem.2019.06.001_bib9) 2018; 137 Rojo (10.1016/j.jorganchem.2019.06.001_bib30) 2003; 9 Franken (10.1016/j.jorganchem.2019.06.001_bib21) 1997; 62 Kirby (10.1016/j.jorganchem.2019.06.001_bib35) 2013; 1834 (10.1016/j.jorganchem.2019.06.001_bib1) 2018; vol. 865 Grüner (10.1016/j.jorganchem.2019.06.001_bib20) 1998; 9 Hawthorne (10.1016/j.jorganchem.2019.06.001_bib8) 1965; 87 DuBay (10.1016/j.jorganchem.2019.06.001_bib14) 1994; 59 Akiyama (10.1016/j.jorganchem.2019.06.001_bib16) 2014; 25 Grüner (10.1016/j.jorganchem.2019.06.001_bib12) 2012 Ruben (10.1016/j.jorganchem.2019.06.001_bib28) 2008; 130 Janoušek (10.1016/j.jorganchem.2019.06.001_bib22) 1981; 46 Farràs (10.1016/j.jorganchem.2019.06.001_bib10) 2012; 41 Plešek (10.1016/j.jorganchem.2019.06.001_bib17) 2002; 67 Plesek (10.1016/j.jorganchem.2019.06.001_bib18) 1997; 62 Wadsworth (10.1016/j.jorganchem.2019.06.001_bib32) 1974; 39 Kirby (10.1016/j.jorganchem.2019.06.001_bib34) 2011; 17 Plešek (10.1016/j.jorganchem.2019.06.001_bib23) 2002; 657 Carvalho (10.1016/j.jorganchem.2019.06.001_bib26) 2015; 13 Leśnikowski (10.1016/j.jorganchem.2019.06.001_bib13) 2016; 59 (10.1016/j.jorganchem.2019.06.001_bib2) 2015; vol. 798 Hosmane (10.1016/j.jorganchem.2019.06.001_bib3) 2018 Plesek (10.1016/j.jorganchem.2019.06.001_bib19) 1976; 41 Dash (10.1016/j.jorganchem.2019.06.001_bib5) 2017 |
| References_xml | – year: 2007 ident: bib7 publication-title: Comprehensive Organometallic Chemistry III – volume: 41 start-page: 3509 year: 1976 end-page: 3515 ident: bib19 article-title: Zwitterionic compounds of 8,8’-X(C2b9h10)2co series with monoatomic O, S, Se, Te, N bridges between carborane ligands publication-title: Collect. Czechoslov. Chem. Commun. contributor: fullname: Wright – volume: 39 start-page: 984 year: 1974 end-page: 989 ident: bib32 article-title: Nucleophilic substitution at phosphorus. Phosphorothioates publication-title: J. Org. Chem. contributor: fullname: Tsay – start-page: 229 year: 2011 end-page: 265 ident: bib11 article-title: Combined processes for high level radioactive waste separations: UNEX and other extraction processes publication-title: Adv. Sep. Tech. Nucl. Fuel Reprocess. Radioact. Waste Treat contributor: fullname: Yu Shadrin – start-page: 849 year: 2017 end-page: 850 ident: bib5 article-title: Cobalt bis(dicarbollide) anion and its derivatives publication-title: J. Organomet. Chem. contributor: fullname: Hosmane – volume: 657 start-page: 59 year: 2002 end-page: 70 ident: bib23 article-title: Functionalized cobalt bis(dicarbollide) ions as selective extraction reagents for removal of M2+ and M3+ cations from nuclear waste, crystal and molecular structures of the [8,8′-μ-CIP(O)(O)2(1,2-C2B9H10)2-3,3′-Co]HN(C2H5)3 and [8,8′-μ-Et2NP(O)(O)2(1,2-C2B9H10)2-3,3′-Co](HN(CH3)3) publication-title: J. Organomet. Chem. contributor: fullname: Rais – volume: 0 start-page: 1172 year: 1970 end-page: 1182 ident: bib31 article-title: The reactivity of phosphate esters. Multiple structure-reactivity correlations for the reactions of triesters with nucleophiles publication-title: J. Chem. Soc. B Phys. Org. contributor: fullname: Kirby – volume: 1834 start-page: 454 year: 2013 end-page: 463 ident: bib35 article-title: New light on phosphate transfer from triesters publication-title: Biochim. Biophys. Acta Protein Proteonomics contributor: fullname: Nome – volume: 133 start-page: 16537 year: 2011 end-page: 16552 ident: bib29 article-title: Relaxed but highly compact diansa metallacyclophanes publication-title: J. Am. Chem. Soc. contributor: fullname: Viñas – volume: 41 start-page: 3445 year: 2012 ident: bib10 article-title: Metallacarboranes and their interactions: theoretical insights and their applicability publication-title: Chem. Soc. Rev. contributor: fullname: Teixidor – volume: vol. 798 year: 2015 ident: bib2 article-title: Organometallic chemistry of polyhedral boranes and carboranes: synthesis, theory, and application publication-title: Special Issue in Journal of Organometallic Chemistry – volume: 46 start-page: 2818 year: 1981 end-page: 2833 ident: bib22 article-title: Synthesis and characteristics of sulfur interligand bridge-derivatives and of some S-substituted compounds in the (C2B9H11)2Co- series. Conformations of (C2B9H11)2Mx- metallocarboranes publication-title: Collect. Czechoslov. Chem. Commun. contributor: fullname: Wright – volume: 106 start-page: 3252 year: 2006 end-page: 3278 ident: bib33 article-title: Enzymatic mechanisms of phosphate and sulfate transfer publication-title: Chem. Rev. contributor: fullname: Hengge – volume: 649 start-page: 181 year: 2002 end-page: 190 ident: bib36 article-title: Syntheses of the B(8)-hydroxy- and B(8,8′)-dihydroxy-derivatives of the bis(1,2-dicarbollido)-3-cobalt(1-)ate ion by its reductive acetoxylation and hydroxylation: molecular structure of [8,8′-μ-CH3C(O)2(1,2-C2B9H10)2-3-Co]0 zwitterion determined by X-ray diffraction analysis publication-title: J. Organomet. Chem. contributor: fullname: Císařová – volume: 59 start-page: 7738 year: 2016 end-page: 7758 ident: bib13 article-title: Challenges and opportunities for the application of boron clusters in drug design publication-title: J. Med. Chem. contributor: fullname: Leśnikowski – volume: 67 start-page: 569 year: 2002 end-page: 576 ident: bib17 article-title: Cobalt bis(1,2-dicarbollide) ion with a disulfur bridge between B(8) and B(8′). X-ray structure, absolute configuration of one enantiomer, and implications publication-title: Collect. Czechoslov. Chem. Commun. contributor: fullname: Bačkovský – volume: 9 start-page: 79 year: 1998 end-page: 88 ident: bib20 article-title: Resolution of the [6,6’-μ-(CH3)2P-(1,7-(C2B9H10)2)-2-Co] bridged cobaltacarborane to enantiomers pure by chiral HPLC, circular dichroism spectra and absolute configurations by X-ray diffraction publication-title: Tetrahedron Asymmetry contributor: fullname: Plešek – volume: 130 start-page: 3349 year: 2008 end-page: 3358 ident: bib28 article-title: Anomeric effect in “high energy” phosphate bonds. Selective destabilization of the scissile bond and modulation of the exothermicity of hydrolysis publication-title: J. Am. Chem. Soc. contributor: fullname: Evanseck – volume: 13 start-page: 5391 year: 2015 end-page: 5398 ident: bib26 article-title: Understanding thio-effects in simple phosphoryl systems: role of solvent effects and nucleophile charge publication-title: Org. Biomol. Chem. contributor: fullname: Kamerlin – volume: 200–202 start-page: 773 year: 2000 end-page: 811 ident: bib4 article-title: Metallacarboranes in the new millennium publication-title: Coord. Chem. Rev. contributor: fullname: Grimes – volume: 70 start-page: 8437 year: 2005 end-page: 8442 ident: bib25 article-title: The thermodynamics of phosphate versus phosphorothioate ester hydrolysis publication-title: J. Org. Chem. contributor: fullname: Hengge – volume: 62 start-page: 1070 year: 1997 end-page: 1079 ident: bib21 article-title: Cobaltacarboranes with intramolecular monophosphorus bridges 8,8’-μ-Me2P(1,2-C2B9H10)2-3-Co, 6,6’-μ-Me2P(1,7-C2B9H10)2-2-Co and the respective non-bridged trimethylphosphine derivatives (8-me3P-1,2-C2B9H10)-3-Co-(1,2-C2B9H11) and (6-me3P-1,7-C2B9H10)-2-Co publication-title: Collect. Czechoslov. Chem. Commun. contributor: fullname: Semrau – start-page: 463 year: 2012 end-page: 490 ident: bib12 article-title: Recent progress in extraction agents based on cobalt bis(dicarbollides) for partitioning of radionuclides from high-level nuclear waste publication-title: Boron Sci. New Technol. Appl. N contributor: fullname: Bubeníková – volume: 59 start-page: 6898 year: 1994 end-page: 6899 ident: bib14 article-title: Lithium cobalt-bis-dicarbollide: a novel Lewis acid catalyst for the conjugate addition of silyl ketene acetals to hindered .alpha.,.beta.-Unsaturated carbonyl compounds publication-title: J. Org. Chem. contributor: fullname: Todd – volume: 9 start-page: 4311 year: 2003 end-page: 4323 ident: bib30 article-title: Relevance of the electronegativity of boron inη5-coordinating ligands: regioselective monoalkylation and monoarylation in cobaltabisdicarbollide[3,3′-Co(1,2-C2B9H11)2]− clusters publication-title: Chem. Eur J. contributor: fullname: Sillanpää – volume: 137 start-page: 92 year: 2018 ident: bib9 article-title: Remarkable aromaticity of cobalt bis(dicarbollide) derivatives: a NICS study publication-title: Theor. Chem. Acc. contributor: fullname: Junqueira – volume: vol. 865 year: 2018 ident: bib1 article-title: Organometallic chemistry of boranes and carboranes (to be dedicated to professor Narayan Hosmane) publication-title: Special Issue in Journal of Organometallic Chemistry – volume: 25 start-page: 795 year: 2014 end-page: 798 ident: bib16 article-title: Phosphoric acid bridged cobalt bis(dicarbollide) ion as a highly efficient catalyst for the organocatalytic hydrogenation of ketimines publication-title: Synlett contributor: fullname: Lesnikowski – year: 2018 ident: bib3 article-title: Handbook of Boron Science contributor: fullname: Eagling – volume: 62 start-page: 884 year: 1997 end-page: 893 ident: bib18 article-title: Synthesis and properties of cobaltacarboranes with substituted monoatomic bridges between ligands of the 6,6’-mu-RnE(1,7-C2B9H10)(2)-2-Co type publication-title: Collect. Czechoslov. Chem. Commun. contributor: fullname: Holub – volume: 17 start-page: 14996 year: 2011 end-page: 15004 ident: bib34 article-title: Activating water: important effects of non-leaving groups on the hydrolysis of phosphate triesters publication-title: Chem. Eur J. contributor: fullname: Nome – volume: 58 start-page: 2936 year: 1993 end-page: 2943 ident: bib24 article-title: Asymmetric cobaltacarboranes [6,6’-μ-R-S(1,7-C2B9H10)2-2-Co] with a monosulfur bridge between ligands and HPLC resolution of the enantiomers publication-title: Collect. Czechoslov. Chem. Commun. contributor: fullname: Votavová – start-page: 47 year: 2012 end-page: 65 ident: bib27 article-title: Thio effects as a tool for mechanistic studies of the cleavage of RNA phosphodiester bonds: the chemical basis publication-title: From Nucleic Acids Seq. To Mol. Med contributor: fullname: Lönnberg – volume: 64 start-page: 783 year: 2002 end-page: 805 ident: bib6 article-title: Chemistry of cobalt bis(dicarbollides). A review publication-title: Collect. Czechoslov. Chem. Commun. contributor: fullname: Bregadze – volume: 37 start-page: 8707 year: 1996 end-page: 8710 ident: bib15 article-title: Lithium cobalt-bis-dicarbollide catalyzed substitution reactions of allylic acetates publication-title: Tetrahedron Lett. contributor: fullname: Todd – volume: 87 start-page: 1818 year: 1965 end-page: 1819 ident: bib8 article-title: Carbametallic boron hydride derivatives. I. Apparent analogs of ferrocene and ferricinium ion publication-title: J. Am. Chem. Soc. contributor: fullname: Wegner – volume: vol. 798 year: 2015 ident: 10.1016/j.jorganchem.2019.06.001_bib2 article-title: Organometallic chemistry of polyhedral boranes and carboranes: synthesis, theory, and application – start-page: 849 year: 2017 ident: 10.1016/j.jorganchem.2019.06.001_bib5 article-title: Cobalt bis(dicarbollide) anion and its derivatives publication-title: J. Organomet. Chem. contributor: fullname: Dash – volume: 59 start-page: 7738 year: 2016 ident: 10.1016/j.jorganchem.2019.06.001_bib13 article-title: Challenges and opportunities for the application of boron clusters in drug design publication-title: J. Med. Chem. doi: 10.1021/acs.jmedchem.5b01932 contributor: fullname: Leśnikowski – volume: 9 start-page: 79 year: 1998 ident: 10.1016/j.jorganchem.2019.06.001_bib20 article-title: Resolution of the [6,6’-μ-(CH3)2P-(1,7-(C2B9H10)2)-2-Co] bridged cobaltacarborane to enantiomers pure by chiral HPLC, circular dichroism spectra and absolute configurations by X-ray diffraction publication-title: Tetrahedron Asymmetry doi: 10.1016/S0957-4166(97)00605-8 contributor: fullname: Grüner – volume: 106 start-page: 3252 year: 2006 ident: 10.1016/j.jorganchem.2019.06.001_bib33 article-title: Enzymatic mechanisms of phosphate and sulfate transfer publication-title: Chem. Rev. doi: 10.1021/cr050287o contributor: fullname: Cleland – volume: 133 start-page: 16537 year: 2011 ident: 10.1016/j.jorganchem.2019.06.001_bib29 article-title: Relaxed but highly compact diansa metallacyclophanes publication-title: J. Am. Chem. Soc. doi: 10.1021/ja205850p contributor: fullname: Farràs – volume: vol. 865 year: 2018 ident: 10.1016/j.jorganchem.2019.06.001_bib1 article-title: Organometallic chemistry of boranes and carboranes (to be dedicated to professor Narayan Hosmane) – volume: 1834 start-page: 454 year: 2013 ident: 10.1016/j.jorganchem.2019.06.001_bib35 article-title: New light on phosphate transfer from triesters publication-title: Biochim. Biophys. Acta Protein Proteonomics doi: 10.1016/j.bbapap.2012.04.010 contributor: fullname: Kirby – volume: 87 start-page: 1818 year: 1965 ident: 10.1016/j.jorganchem.2019.06.001_bib8 article-title: Carbametallic boron hydride derivatives. I. Apparent analogs of ferrocene and ferricinium ion publication-title: J. Am. Chem. Soc. doi: 10.1021/ja01086a053 contributor: fullname: Hawthorne – year: 2018 ident: 10.1016/j.jorganchem.2019.06.001_bib3 contributor: fullname: Hosmane – volume: 59 start-page: 6898 year: 1994 ident: 10.1016/j.jorganchem.2019.06.001_bib14 article-title: Lithium cobalt-bis-dicarbollide: a novel Lewis acid catalyst for the conjugate addition of silyl ketene acetals to hindered .alpha.,.beta.-Unsaturated carbonyl compounds publication-title: J. Org. Chem. doi: 10.1021/jo00102a009 contributor: fullname: DuBay – volume: 62 start-page: 1070 year: 1997 ident: 10.1016/j.jorganchem.2019.06.001_bib21 article-title: Cobaltacarboranes with intramolecular monophosphorus bridges 8,8’-μ-Me2P(1,2-C2B9H10)2-3-Co, 6,6’-μ-Me2P(1,7-C2B9H10)2-2-Co and the respective non-bridged trimethylphosphine derivatives (8-me3P-1,2-C2B9H10)-3-Co-(1,2-C2B9H11) and (6-me3P-1,7-C2B9H10)-2-Co publication-title: Collect. Czechoslov. Chem. Commun. doi: 10.1135/cccc19971070 contributor: fullname: Franken – volume: 70 start-page: 8437 year: 2005 ident: 10.1016/j.jorganchem.2019.06.001_bib25 article-title: The thermodynamics of phosphate versus phosphorothioate ester hydrolysis publication-title: J. Org. Chem. doi: 10.1021/jo0511997 contributor: fullname: Purcell – volume: 67 start-page: 569 year: 2002 ident: 10.1016/j.jorganchem.2019.06.001_bib17 article-title: Cobalt bis(1,2-dicarbollide) ion with a disulfur bridge between B(8) and B(8′). X-ray structure, absolute configuration of one enantiomer, and implications publication-title: Collect. Czechoslov. Chem. Commun. doi: 10.1135/cccc20020569 contributor: fullname: Plešek – volume: 200–202 start-page: 773 year: 2000 ident: 10.1016/j.jorganchem.2019.06.001_bib4 article-title: Metallacarboranes in the new millennium publication-title: Coord. Chem. Rev. doi: 10.1016/S0010-8545(00)00262-9 contributor: fullname: Grimes – volume: 46 start-page: 2818 year: 1981 ident: 10.1016/j.jorganchem.2019.06.001_bib22 article-title: Synthesis and characteristics of sulfur interligand bridge-derivatives and of some S-substituted compounds in the (C2B9H11)2Co- series. Conformations of (C2B9H11)2Mx- metallocarboranes publication-title: Collect. Czechoslov. Chem. Commun. doi: 10.1135/cccc19812818 contributor: fullname: Janoušek – volume: 13 start-page: 5391 year: 2015 ident: 10.1016/j.jorganchem.2019.06.001_bib26 article-title: Understanding thio-effects in simple phosphoryl systems: role of solvent effects and nucleophile charge publication-title: Org. Biomol. Chem. doi: 10.1039/C5OB00309A contributor: fullname: Carvalho – volume: 649 start-page: 181 year: 2002 ident: 10.1016/j.jorganchem.2019.06.001_bib36 publication-title: J. Organomet. Chem. doi: 10.1016/S0022-328X(02)01115-4 contributor: fullname: Plešek – year: 2007 ident: 10.1016/j.jorganchem.2019.06.001_bib7 – start-page: 463 year: 2012 ident: 10.1016/j.jorganchem.2019.06.001_bib12 article-title: Recent progress in extraction agents based on cobalt bis(dicarbollides) for partitioning of radionuclides from high-level nuclear waste contributor: fullname: Grüner – volume: 62 start-page: 884 year: 1997 ident: 10.1016/j.jorganchem.2019.06.001_bib18 article-title: Synthesis and properties of cobaltacarboranes with substituted monoatomic bridges between ligands of the 6,6’-mu-RnE(1,7-C2B9H10)(2)-2-Co type publication-title: Collect. Czechoslov. Chem. Commun. doi: 10.1135/cccc19970884 contributor: fullname: Plesek – volume: 25 start-page: 795 year: 2014 ident: 10.1016/j.jorganchem.2019.06.001_bib16 article-title: Phosphoric acid bridged cobalt bis(dicarbollide) ion as a highly efficient catalyst for the organocatalytic hydrogenation of ketimines publication-title: Synlett doi: 10.1055/s-0033-1340847 contributor: fullname: Akiyama – volume: 0 start-page: 1172 year: 1970 ident: 10.1016/j.jorganchem.2019.06.001_bib31 article-title: The reactivity of phosphate esters. Multiple structure-reactivity correlations for the reactions of triesters with nucleophiles publication-title: J. Chem. Soc. B Phys. Org. doi: 10.1039/J29700001172 contributor: fullname: Khan – volume: 41 start-page: 3509 year: 1976 ident: 10.1016/j.jorganchem.2019.06.001_bib19 article-title: Zwitterionic compounds of 8,8’-X(C2b9h10)2co series with monoatomic O, S, Se, Te, N bridges between carborane ligands publication-title: Collect. Czechoslov. Chem. Commun. doi: 10.1135/cccc19763509 contributor: fullname: Plesek – volume: 58 start-page: 2936 year: 1993 ident: 10.1016/j.jorganchem.2019.06.001_bib24 article-title: Asymmetric cobaltacarboranes [6,6’-μ-R-S(1,7-C2B9H10)2-2-Co] with a monosulfur bridge between ligands and HPLC resolution of the enantiomers publication-title: Collect. Czechoslov. Chem. Commun. doi: 10.1135/cccc19932936 contributor: fullname: Plešek – start-page: 47 year: 2012 ident: 10.1016/j.jorganchem.2019.06.001_bib27 article-title: Thio effects as a tool for mechanistic studies of the cleavage of RNA phosphodiester bonds: the chemical basis contributor: fullname: Ora – volume: 130 start-page: 3349 year: 2008 ident: 10.1016/j.jorganchem.2019.06.001_bib28 article-title: Anomeric effect in “high energy” phosphate bonds. Selective destabilization of the scissile bond and modulation of the exothermicity of hydrolysis publication-title: J. Am. Chem. Soc. doi: 10.1021/ja073652x contributor: fullname: Ruben – volume: 137 start-page: 92 year: 2018 ident: 10.1016/j.jorganchem.2019.06.001_bib9 article-title: Remarkable aromaticity of cobalt bis(dicarbollide) derivatives: a NICS study publication-title: Theor. Chem. Acc. doi: 10.1007/s00214-018-2272-6 contributor: fullname: Junqueira – volume: 64 start-page: 783 year: 2002 ident: 10.1016/j.jorganchem.2019.06.001_bib6 article-title: Chemistry of cobalt bis(dicarbollides). A review publication-title: Collect. Czechoslov. Chem. Commun. doi: 10.1135/cccc19990783 contributor: fullname: Sivaev – start-page: 229 year: 2011 ident: 10.1016/j.jorganchem.2019.06.001_bib11 article-title: Combined processes for high level radioactive waste separations: UNEX and other extraction processes contributor: fullname: Romanovskiy – volume: 17 start-page: 14996 year: 2011 ident: 10.1016/j.jorganchem.2019.06.001_bib34 article-title: Activating water: important effects of non-leaving groups on the hydrolysis of phosphate triesters publication-title: Chem. Eur J. doi: 10.1002/chem.201101926 contributor: fullname: Kirby – volume: 9 start-page: 4311 year: 2003 ident: 10.1016/j.jorganchem.2019.06.001_bib30 article-title: Relevance of the electronegativity of boron inη5-coordinating ligands: regioselective monoalkylation and monoarylation in cobaltabisdicarbollide[3,3′-Co(1,2-C2B9H11)2]− clusters publication-title: Chem. Eur J. doi: 10.1002/chem.200304970 contributor: fullname: Rojo – volume: 39 start-page: 984 year: 1974 ident: 10.1016/j.jorganchem.2019.06.001_bib32 article-title: Nucleophilic substitution at phosphorus. Phosphorothioates publication-title: J. Org. Chem. doi: 10.1021/jo00921a027 contributor: fullname: Wadsworth – volume: 37 start-page: 8707 year: 1996 ident: 10.1016/j.jorganchem.2019.06.001_bib15 article-title: Lithium cobalt-bis-dicarbollide catalyzed substitution reactions of allylic acetates publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(96)02021-7 contributor: fullname: Grieco – volume: 657 start-page: 59 year: 2002 ident: 10.1016/j.jorganchem.2019.06.001_bib23 publication-title: J. Organomet. Chem. doi: 10.1016/S0022-328X(02)01325-6 contributor: fullname: Plešek – volume: 41 start-page: 3445 year: 2012 ident: 10.1016/j.jorganchem.2019.06.001_bib10 article-title: Metallacarboranes and their interactions: theoretical insights and their applicability publication-title: Chem. Soc. Rev. doi: 10.1039/c2cs15338f contributor: fullname: Farràs |
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| Title | Unusual resistance of cobalt bis dicarbollide phosphate and phosphorothioate bridged esters towards alkaline hydrolysis: The “metallacarborane effect” |
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