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Inter- or intramolecular N···H-O or N-H···O Hydrogen bonding in 1,3-Amino-alpha/beta-naphthols : an experimental NMR and computational study

  • The existence of intermolecular or intramolecular N···H;O or N;H···O hydrogen bonding in three series (series 1, substituted 1-aminoalkyl-2-naphthols: R = H, Me, Et, Pr, i-Pr; series 2, substituted 1-;- aminobenzyl-2-naphthols: H, p-OMe, p-F, p-Cl, p-Br, p-NO2, p-Me; series 3, substituted 2-;-aminobenzyl-1-naphthols: R = H, p-Me, p-F, p-Br, p-OMe, m-NO2, m-Br) are studied by NMR spectroscopy and computed at the DFT level of theory [B3LYP/6-311+G(d,p)]. The correct nature of the H-bond was assigned unequivocally both experimentally and computationally by potential energy scans rotating the involved dihedral angles. We investigated the effects of substituents on the strength of the H-bond by evaluating the corresponding hyperconjugative stabilization energy nlonepair ; ;*X;H and Hammett substituent constant plots. By this means, steric and electronic substituent effects could be easily quantified and separated.

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Author:Anica Lämmermann, István Szatmári, Ferenc Fülöp, Erich Kleinpeter
Document Type:Article
Year of first Publication:2009
Year of Completion:2009
Release Date:2017/03/25
Source:Journal of physical chemistry / A. - ISSN 1089-5639. - e-ISSN 1520-5215. - 113 (2009), 21, S. 6197 - 6205
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
Peer Review:Referiert