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Volumn 9, Issue 10, 2011, Pages 3636-3657

Effect of substituents on the stabilities of multiply-substituted carbon-centered radicals

Author keywords

[No Author keywords available]

Indexed keywords

ADDITIVITY; BASIS SETS; BOND DISSOCIATION ENERGIES; CARBON-CENTERED RADICALS; CLOSED SHELLS; COMPOSITE METHOD; CURRENT TEST; EXPERIMENTAL DATA; MOLECULE INTERACTIONS; RADICAL INTERACTIONS; RADICAL STABILIZATION ENERGY; STABLE RADICALS; SUBSTITUTED CARBONS;

EID: 79955388137     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c1ob05196b     Document Type: Article
Times cited : (60)

References (100)
  • 56
    • 33748349486 scopus 로고    scopus 로고
    • I. Prigogine and S. A. Rice, ed., John Wiley & Sons, Inc., 101
    • J. F. Stanton, and J. Gauss, in Advances in Chemical Physics, I. Prigogine, and, S. A. Rice, ed., John Wiley & Sons, Inc., 2003, 125, p 101
    • (2003) Advances in Chemical Physics
    • Stanton, J.F.1    Gauss, J.2
  • 57
    • 0033449808 scopus 로고    scopus 로고
    • I. Lipkowitz and D. B. Boyd, ed., Wiley-VCH, New York, We note that the single-point energy calculations employing DFT procedures in ref. 9b and 9c used RB3-LYP(6-31G(d) geometries. In the present study, we use UB3-LYP(6-31G(d) geometries and the assessment was repeated for a selected set of functionals. The results are given in Table S1 of the Supporting Information
    • T. Bally, and W. T. Borden, in Reviews in Computational Chemistry, I. Lipkowitz, and, D. B. Boyd, ed., Wiley-VCH, New York, 1999, Vol. 13
    • (1999) Reviews in Computational Chemistry
    • Bally, T.1    Borden, W.T.2
  • 80
    • 0042590007 scopus 로고    scopus 로고
    • Positive hyperconjugation corresponds to donation from a C-X σ-orbital into an adjacent acceptor orbital while negative hyperconjugation corresponds to donation from an n or π-orbital into an adjacent σ* C-X orbital. See, for example:
    • K. Pius M. Jain J. Chandrasekhar THEOCHEM 1996 361 191
    • (1996) THEOCHEM , vol.361 , pp. 191
    • Pius, K.1    Jain, M.2    Chandrasekhar, J.3
  • 81
    • 0000151857 scopus 로고
    • and references therein. Also see ref. 37c For detailed explanations of the hyperconjugative ability of sigma bonds and on the π-donor abilities of hetero atoms, see:
    • P. V. Schleyer A. J. Kos Tetrahedron 1983 39 1141
    • (1983) Tetrahedron , vol.39 , pp. 1141
    • Schleyer, P.V.1    Kos, A.J.2
  • 100
    • 84981893721 scopus 로고
    • See ref. 41. Separately, it has been suggested 13 that radicals of this kind prefer pyramidalization, as this decreases the energy gap between the SOMO and the lone pair orbital of the π-donor. However, since pyramidalization decreases the effective overlap between the SOMO and the heteroatom lone pair, it has been argued in ref. 13 that the overall result will represent a compromise between these two effects
    • C. Rüchardt Angew. Chem., Int. Ed. Engl. 1970 9 830
    • (1970) Angew. Chem., Int. Ed. Engl. , vol.9 , pp. 830
    • Rüchardt, C.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.