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Volumn 75, Issue 15, 2010, Pages 4957-4963

Erratum: Nucleophilicity and site selectivity of commonly used arenes and heteroarenes (Journal of Organic Chemistry (2010) 75 (4957-4963) DOI: 10.1021/jo100425a);Nucleophilicity and site selectivity of commonly used arenes and heteroarenes

Author keywords

[No Author keywords available]

Indexed keywords

INVERSE PROBLEMS; SUBSTITUTION REACTIONS;

EID: 77955144553     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo2007225     Document Type: Erratum
Times cited : (107)

References (60)
  • 34
    • 0037181996 scopus 로고    scopus 로고
    • It may be noted that while the inverse relationship between electrophilicity and nucleophilicity have been successfully utilized in this set of molecules, providing good correlation between experimental and computed results, that does not mean that a weak electrophile automatically becomes a strong nucleophile and vice versa. Indeed in many studies involving organic compounds this inverse relationship did not work. For recent demonstration of such a view please see
    • It may be noted that while the inverse relationship between electrophilicity and nucleophilicity have been successfully utilized in this set of molecules, providing good correlation between experimental and computed results, that does not mean that a weak electrophile automatically becomes a strong nucleophile and vice versa. Indeed in many studies involving organic compounds this inverse relationship did not work. For recent demonstration of such a view please see: Domingo, L. R.; Aurell, M. J.; Perez, P.; Contreras, R. Tetrahedron 2002, 58, 4417-4423
    • (2002) Tetrahedron , vol.58 , pp. 4417-4423
    • Domingo, L.R.1    Aurell, M.J.2    Perez, P.3    Contreras, R.4
  • 35
    • 0037074619 scopus 로고    scopus 로고
    • We thank one of the reviewers for raising this important issue
    • Domingo, L. R.; Arno, M.; Contreras, R.; Perez, P. J. Phys. Chem. A 2002, 106, 952-961 We thank one of the reviewers for raising this important issue.
    • (2002) J. Phys. Chem. A , vol.106 , pp. 952-961
    • Domingo, L.R.1    Arno, M.2    Contreras, R.3    Perez, P.4
  • 40
    • 77955141171 scopus 로고    scopus 로고
    • Please see the Supporting Information for details
    • Please see the Supporting Information for details.
  • 49
    • 77955138726 scopus 로고    scopus 로고
    • It may be noted that while the Hammett correlation coefficients are nearly similar for both methods III and IV, we have found that method III correctly predicts the higher nucleophilicity of thiophenol than ethylbenzene, whereas method IV wrongly predicts the opposite. Thus the method III derived classification of moderate nucleophiles at the boundary of alkylbenzene correlates well with experiment
    • It may be noted that while the Hammett correlation coefficients are nearly similar for both methods III and IV, we have found that method III correctly predicts the higher nucleophilicity of thiophenol than ethylbenzene, whereas method IV wrongly predicts the opposite. Thus the method III derived classification of moderate nucleophiles at the boundary of alkylbenzene correlates well with experiment.
  • 56
    • 0000140589 scopus 로고
    • The reader may note that the local nucleophilicity indices do not conform well in predicting intermolecular reactivity order in a group of arenes and heteroarenes containing an electron-withdrawing group. Geerling et a.l has also observed that Fukui function works less well for arenes having deactivating functional groups. Please see
    • The reader may note that the local nucleophilicity indices do not conform well in predicting intermolecular reactivity order in a group of arenes and heteroarenes containing an electron-withdrawing group. Geerling et a.l has also observed that Fukui function works less well for arenes having deactivating functional groups. Please see: Langenaeker, W.; De Proft, F.; Geerlings, P. J. Phys. Chem. 1995, 99, 6424-6431
    • (1995) J. Phys. Chem. , vol.99 , pp. 6424-6431
    • Langenaeker, W.1    De Proft, F.2    Geerlings, P.3
  • 57
    • 0000171532 scopus 로고    scopus 로고
    • We thank one of the reviewers for pointing this out to us
    • Langenaeker, W.; De Proft, F.; Geerlings THEOCHEM 1996, 362, 175-179 We thank one of the reviewers for pointing this out to us.
    • (1996) Geerlings THEOCHEM , vol.362 , pp. 175-179
    • Langenaeker, W.1    De Proft, F.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.