Effect of a Substituent on the Properties of Salicylaldehyde Hydrazone Derivatives
The present study investigates the effect of the substitution of salicylaldehyde hydrazones at two selected positions, i.e., the para-position with regard to the proton-donating and proton-accepting centers forming the hydrogen bridge. A detailed analysis of structural data obtained by theoretical a...
Saved in:
| Published in: | Journal of organic chemistry Vol. 88; no. 4; pp. 2132 - 2139 |
|---|---|
| Main Authors: | , , , |
| Format: | Journal Article |
| Language: | English |
| Published: |
United States
American Chemical Society
17-02-2023
|
| Online Access: | Get full text |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| Summary: | The present study investigates the effect of the substitution of salicylaldehyde hydrazones at two selected positions, i.e., the para-position with regard to the proton-donating and proton-accepting centers forming the hydrogen bridge. A detailed analysis of structural data obtained by theoretical approaches and X-ray experiments, together with original resonance Hammett’s constants, indicates that the strength of the intramolecular hydrogen bonding present in salicylaldehyde hydrazones can be selectively modulated by substitution of the parent molecular system with the chemical group of known π-electron-donating or -accepting properties. Our findings provide an insight into planning synthesis pathways for salicylaldehyde hydrazone species and predicting their result with regard to their H-bonding and related physical and chemical properties. |
|---|---|
| Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
| ISSN: | 0022-3263 1520-6904 |
| DOI: | 10.1021/acs.joc.2c02547 |