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N−H‐Type Excited‐State Proton Transfer in Compounds Possessing a Seven‐Membered‐Ring Intramolecular Hydrogen Bond
Author(s) -
Chen YiAn,
Meng FanYi,
Hsu YenHao,
Hung ChengHsien,
Chen ChiLin,
Chung KunYou,
Tang WeiFeng,
Hung WenYi,
Chou PiTai
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201602425
Subject(s) - intramolecular force , tautomer , chemistry , hydrogen bond , substituent , ring (chemistry) , proton , photochemistry , excited state , molecule , stereochemistry , organic chemistry , physics , quantum mechanics , nuclear physics
A series of compounds containing 5‐(2‐aminobenzylidene)‐2,3‐dimethyl‐3,5‐dihydro‐4 H ‐imidazol‐4‐one ( o ‐ABDI ) as the core chromophore with a seven‐membered‐ring N−H‐type intramolecular hydrogen bond have been synthesized and characterized. The acidity of the N−H proton and thus the hydrogen‐bond strength can be fine‐tuned by replacing one of the amino hydrogen atoms by a substituent R, the acidity increasing with increasing electron‐withdrawing strength of R, that is, in the order H
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