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Quantum Mechanical Calculations of Conformationally Relevant 1 H and 13 C NMR Chemical Shifts of N‐, O‐, and S‐Substituted Calixarene Systems
Author(s) -
Bifulco Giuseppe,
Riccio Raffaele,
Gaeta Carmine,
Neri Placido
Publication year - 2007
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.200700238
Subject(s) - calixarene , dihedral angle , chemistry , molecule , computational chemistry , crystallography , cyclophane , crystal structure , hydrogen bond , organic chemistry
QM GIAO calculations of 13 C and 1 H chemical shift values of the ArCH 2 Ar group in N‐, O‐, and S‐substituted calixarene systems were performed with a hybrid DFT functional MPW1PW91 and 6‐31G(d,p) basis set. A good reproduction of experimental data was obtained for some representative calixarenes and for a series of simplified calixarene models. This allowed the derivation of chemical shift surfaces versus ϕ and χ dihedral angles. The applicability of chemical shift surfaces in the study of calixarene conformational features is illustrated.