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Volumn 24, Issue 6, 2011, Pages 480-491

Concerted SN2 mechanism for the hydrolysis of acid chlorides: Comparisons of reactivities calculated by the density functional theory with experimental data

Author keywords

acid chlorides; DFT calculations; nucleophilic substitution; solvent effect; substituent effect

Indexed keywords

ACID CHLORIDES; DFT CALCULATION; NUCLEOPHILIC SUBSTITUTIONS; SOLVENT EFFECT; SUBSTITUENT EFFECT;

EID: 79958195858     PISSN: 08943230     EISSN: 10991395     Source Type: Journal    
DOI: 10.1002/poc.1790     Document Type: Article
Times cited : (33)

References (88)
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    • (Eds: C. H. Bamford, C. F. H. Tipper), Elsevier, Amsterdam, Vol. 10, Chapter 3.
    • R. J. E. Talbot, Comprehensive Chemical Kinetics (Eds:, C. H. Bamford, C. F. H. Tipper,), Elsevier, Amsterdam, 1973, Vol. 10, Chapter 3, 223-257.
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  • 4
    • 48249121415 scopus 로고    scopus 로고
    • (Eds: M. S. Platz, R. A. Moss, M. Jones Jr.), Wiley, New York.
    • J. P. Guthrie, Review of Reactive Intermediate Chemistry (Eds:, M. S. Platz, R. A. Moss, M. Jones Jr.,), Wiley, New York, 2007, 4-20.
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    • note
    • [1,46].
  • 53
    • 79958215860 scopus 로고    scopus 로고
    • note
    • -1 were calculated for TSs 21a and 22a, respectively, at (B3LYP)/6-31G(d) level of theory in water, at 0°C.
  • 56
    • 79958189994 scopus 로고    scopus 로고
    • note
    • Calculations can be performed only at the medium (B3LYP)/6-31G(d) level of theory, because the negative charge of the carbonyl oxygen becomes very small, and no hydrogen bond is formed between C=O group and the water molecule when calculations are carried out at the higher (B3LYP)/6-311+G(d,p) level of theory.
  • 57
    • 79958218140 scopus 로고    scopus 로고
    • note
    • -1 in water, at -10°C.
  • 68
    • 79958186235 scopus 로고    scopus 로고
    • note
    • [47] in acetone-water mixtures.
  • 70
    • 79958183156 scopus 로고    scopus 로고
    • note
    • ‡.
  • 71
    • 79958184540 scopus 로고    scopus 로고
    • Reference 45, pp.170-177
    • Reference 45, pp.170-177.
  • 73
    • 79958208541 scopus 로고    scopus 로고
    • Reference 46, pp. 449-453
    • Reference 46, pp. 449-453.
  • 84
    • 79958185581 scopus 로고    scopus 로고
    • Available at: http://www.gaussian.com/g-whitepap/thermo/thermo.pdf


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.