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Intra‐ and intermolecular NH···O hydrogen bonds in pyrrolyl derivatives of indane‐1,3‐dione – experimental and theoretical study
Author(s) -
Sigalov M.,
Shainyan B.,
Chipani.,
Ushakov I.,
Shulunova A.
Publication year - 2009
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.1573
Subject(s) - chemistry , intramolecular force , intermolecular force , hydrogen bond , conformational isomerism , molecule , pyridine , quantum chemical , indane , acetone , computational chemistry , crystallography , medicinal chemistry , stereochemistry , organic chemistry
2‐(Pyrrol‐2‐ylmethylene)‐1,3‐indandione ( 4 ) and 2‐(pyrrol‐2‐ylmethylene)‐3‐dicyanomethylidene‐1‐indanone ( 5 ) were synthesized. Multinuclear and 2D‐NMR, IR, UV spectroscopic investigations as well as quantum chemical calculations showed the presence of strong hydrogen bonding in these molecules. For both molecules, the presence of two conformers, with and without H‐bond, was experimentally detected in the basic solvents (DMSO, acetone, pyridine) and the solvate complexes were theoretically calculated. Specific behavior of the intramolecular H‐bonded complexes different from that of the intermolecular H‐complexes is discussed. Copyright © 2009 John Wiley & Sons, Ltd.