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Computational chemical studies of chiral stationary‐phase models: The nature of the Pi interaction in complexes of methyl N ‐(2‐naphthyl) alaninate with N ‐(3,5‐dinitrobenzoyl)leucine n ‐propylamide
Author(s) -
Sabio Michael,
Topiol Sid
Publication year - 1989
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.560360314
Subject(s) - chemistry , basis set , perturbation theory (quantum mechanics) , naphthalene , interaction energy , computational chemistry , stereochemistry , pi , molecule , density functional theory , physics , quantum mechanics , organic chemistry , biochemistry
The pi interaction in complexes of (S)‐methyl N ‐(2‐naphthyl)alaninate with (S)‐ and (R)‐ N ‐(3,5‐dinitrobenzoyl)leucine n ‐propylamide was investigated with Hartree–Fock and second‐order Møller–Plesset perturbation theory calculations using the STO ‐3G basis set. For each complex, the geometry of the model of the pi interaction (i.e., naphthalene and 1,3‐dinitrobenzene) was derived directly from the complex geometry which was relaxed by the semiempirical quantum‐mechanical AM 1 method. At the level of treatment used herein, our results are in agreement with our earlier AM 1 interaction energy calculations in which the pi interaction, one of the three primary interactions proposed in models of the aforementioned complexes, is attractive and of equal strength (ca. 0.8 kcal/mol) in both complexes.