Display options
Cite
Takahashi O, Kohno Y, Saito K, et al. Prevalence of the alkyl/phenyl-folded conformation in benzylic compounds C6H5CH2-X-R (X=O, CH2, CO, S, SO, SO2): significance of the CH/pi interaction as evidenced by high-level ab initio MO calculations. Chemistry. 2003;9(3):756-62doi: 10.1002/chem.200390084.
Takahashi, O., Kohno, Y., Saito, K., & Nishio, M. (2003). Prevalence of the alkyl/phenyl-folded conformation in benzylic compounds C6H5CH2-X-R (X=O, CH2, CO, S, SO, SO2): significance of the CH/pi interaction as evidenced by high-level ab initio MO calculations. Chemistry (Weinheim an der Bergstrasse, Germany), 9(3), 756-62. https://doi.org/10.1002/chem.200390084
Takahashi, Osamu, et al. "Prevalence of the alkyl/phenyl-folded conformation in benzylic compounds C6H5CH2-X-R (X=O, CH2, CO, S, SO, SO2): significance of the CH/pi interaction as evidenced by high-level ab initio MO calculations." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 9,3 (2003): 756-62. doi: https://doi.org/10.1002/chem.200390084
Takahashi O, Kohno Y, Saito K, Nishio M. Prevalence of the alkyl/phenyl-folded conformation in benzylic compounds C6H5CH2-X-R (X=O, CH2, CO, S, SO, SO2): significance of the CH/pi interaction as evidenced by high-level ab initio MO calculations. Chemistry. 2003 Feb 03;9(3):756-62. doi: 10.1002/chem.200390084. PMID: 12569468.
Copy Download .nbib Format: NLM
Share it on

Chemistry. 2003 Feb 03;9(3):756-62. doi: 10.1002/chem.200390084.

Prevalence of the alkyl/phenyl-folded conformation in benzylic compounds C6H5CH2-X-R (X=O, CH2, CO, S, SO, SO2): significance of the CH/pi interaction as evidenced by high-level ab initio MO calculations.

Chemistry (Weinheim an der Bergstrasse, Germany)

Osamu Takahashi, Yuji Kohno, Ko Saito, Motohiro Nishio

Affiliations

  1. Department of Chemistry, Graduate School of Science Hiroshima University, Kagamiyama, Higashi Hiroshima 739-8526, Japan.

PMID: 12569468 DOI: 10.1002/chem.200390084

Abstract

Ab initio MO calculations were carried out to examine the conformational energies of various benzylic compounds C(6)H(5)CH(2)XR (X=O, CH(2), CO, S, SO, SO(2); R=CH(3), C(2)H(5), iC(3)H(7), tC(4)H(9)) at the MP2/6-311G(d,p)//MP2/6-31G(d) level. Rotamers with R/Ph in gauche relationship are generally more stable than the R/Ph anti rotamers. In these stable geometries, the interatomic distance in the interaction of alpha- or beta-CH in the alkyl group and the ipso-carbon atom of the phenyl ring is short. The computational results are consistent with experimental data from supersonic molecular jet spectroscopy on 3-n-propyltoluene and NMR and crystallographic data on structurally related ketones, sulfoxides, and sulfones. In view of this, the alkyl/phenyl-congested conformation of these compounds has been suggested to be a general phenomenon, rather than an exception. The attractive CH/pi interaction has been suggested to be a dominant factor in determining the conformation of simple aralkyl compounds.

Publication Types