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GIAO‐HF/DFT calculation of 13 C and 15 N chemical shifts for studying tautomerism and intramolecular hydrogen bonding in 2,3‐disubstituted quinoxalines
Author(s) -
Kleinpeter E.,
Hilfert L.,
Koch A.
Publication year - 2000
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 - 10.1002/1099-1395(200008)13:8<473::aid-poc260>3.0.co;2-e
Subject(s) - chemistry , tautomer , intramolecular force , chemical shift , substituent , ab initio , hydrogen bond , computational chemistry , hydrogen , enol , stereochemistry , molecule , organic chemistry , catalysis
Both the 13 C and 15 N chemical shifts of a number of quinoxalines substituted in position 2 with the π‐electron excess 2′‐benzo[ b ]furanyl substituent which has in position 3′ a hydroxy or amino group could be satisfactorily calculated by the GIAO method on the basis of HF and DFT ab initio structures. Thereby both the presence of the intramolecular hydrogen bond —C2=N···H—O—C3′— and —C2N···H—NH—C3′—, respectively, strongly dominating the common plane of resonance of the two heterocyclic moieties, and the preferred enol tautomer could be studied in detail. Copyright © 2000 John Wiley & Sons, Ltd.