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Intramolecular and intermolecular bifurcated hydrogen bonds in 2‐pyrrolyl‐7‐hydroxy‐2‐methylidene‐2,3‐dihydro‐1 H ‐inden‐1‐one
Author(s) -
Chipanii.,
Oznobikhina Larisa P.,
Sigalov Mark V.,
Shainyan Bagrat A.
Publication year - 2019
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.3924
Subject(s) - chemistry , intramolecular force , intermolecular force , hydrogen bond , solvent , photochemistry , proton , acceptor , spectroscopy , solvent effects , crystallography , stereochemistry , molecule , organic chemistry , physics , quantum mechanics , condensed matter physics
Cyclic and linear dimers as well as the solvate H‐bonded complexes of the Z and E isomers of 2‐pyrrolyl‐7‐hydroxy‐2‐methylidene‐2,3‐dihydro‐1 H ‐inden‐1‐one 1 were investigated by theoretical calculations, and their formation was proved by FT‐IR and UV spectroscopy. In dimers, both strengthening and weakening of the intramolecular component of the bifurcated hydrogen bond are observed depending on the type of the formed intermolecular hydrogen bond. The effect of proton donors MeOH, HCN, and proton acceptor DMSO on the intramolecular components in solvent H‐bonded complexes is discussed. A larger energy gap in the 1 ‐ E than in 1 ‐ Z isomer allows to predict photoinduced isomeric transition 1 ‐ Е → 1 ‐ Z in nonpolar aprotic solvents.