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Bowl‐shaped hydrocarbons related to C 60
Author(s) -
Schulman Jerome M.,
Disch Raymond L.
Publication year - 1998
Publication title -
journal of computational chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.907
H-Index - 188
eISSN - 1096-987X
pISSN - 0192-8651
DOI - 10.1002/(sici)1096-987x(19980130)19:2<189::aid-jcc11>3.0.co;2-d
Subject(s) - chemical shift , chemistry , ab initio , computational chemistry , bond length , carbon 13 nmr , ab initio quantum chemistry methods , crystallography , molecule , stereochemistry , organic chemistry , crystal structure
Ab initio studies at the HF/6‐31G* and B3LYP/6‐31G* levels are reported for two bowl‐shaped hydrocarbons related to C 60 : C 30 H 12 and C 36 H 12 , of C 3 and C 3 v symmetry, respectively. The former has an approximate heat of formation of 211 kcal/mol. Bowl‐to‐bowl interconversion may occur through a planar ( C 3 h ) form of ca. 64 kcal/mol greater energy having one imaginary vibrational frequency. The larger C 36 H 12 bowl has a calculated Δ H ° f of 265 kcal/mol. Its HF/6‐31G*, B3LYP/6‐31G*, and MM3 bond lengths are in good agreement with a recent X‐ray structure. Chemical shifts for both compounds calculated by the GIAO method are in good agreement with the measured NMR spectra. The observed 13 C chemical shifts increase with the extent of pyramidalization. © 1998 John Wiley & Sons, Inc. J Comput Chem 19: 189–194, 1998