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Issue 24, 1996
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Nature of the non-bonded (C—H)⋯O interaction of ethers CH3O—(CH2)n—OCH3(n= 4–8)

Abstract

Conformational free energies of dimethoxy ethers CH3O—(CH2)n—OCH3(n= 4–8) were calculated by ab initio molecular orbital calculations at the Hartree–Fock level of theory using the 6-31G* basis set with the electronic correlation effects evaluated using second-order Møller–Plesset theory on the 6-31 + G* basis set. The dimethoxy ethers are model compounds of polyethers [—(CH2)y—O—]x and have been investigated in terms of the non-bonded intramolecular (C—H)⋯O interaction that occurs in the g±g conformations for the C—O/C—C pair. This interaction was found to be attractive (–0.43 kcal mol–1, 1 cal = 4.184 J) only for 1,4-dimethoxybutane (n= 4) and repulsive (0.24–0.77 kcal mol–1) for the other longer ether chains (n[gt-or-equal] 5). The attractive interaction is discussed here in relation to intramolecular (C—H)⋯O hydrogen bonding.

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Article type: Paper
DOI: 10.1039/FT9969204885
Citation: J. Chem. Soc., Faraday Trans., 1996,92, 4885-4888
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    Nature of the non-bonded (C—H)⋯O interaction of ethers CH3O—(CH2)n—OCH3(n= 4–8)

    R. V. Law and Y. Sasanuma, J. Chem. Soc., Faraday Trans., 1996, 92, 4885
    DOI: 10.1039/FT9969204885

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