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Volumn 41, Issue 12, 2000, Pages 2001-2005

A theoretical study of aromaticity in squaramide and oxocarbons

Author keywords

Aromaticity; NMR; Oxocarbon acids and derivatives; Theoretical studies

Indexed keywords

AMMONIA; ANION; CARBON; OXOACID; SQUARAMIDE; SQUARIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0042902817     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00084-8     Document Type: Article
Times cited : (84)

References (31)
  • 1
    • 0004142086 scopus 로고
    • (a) Ed.; Academic Press: New York
    • (a) Oxocarbons; West, R., Ed.; Academic Press: New York, 1980.
    • (1980) Oxocarbons
    • West, R.1
  • 23
    • 0001280099 scopus 로고    scopus 로고
    • Schleyer, P. v. R.; Allinger, N. L.; Clark, T.; Gasteiger, J.; Kollman, P. A.; Schaefer III, H. F.; Schreiner, P. R., Eds.; John Wiley & Sons: Chichester
    • Fleisher, U.; van Wüllen, C.; Kutzelnigg, W. In Encyclopedia of Computational Chemistry; Schleyer, P. v. R.; Allinger, N. L.; Clark, T.; Gasteiger, J.; Kollman, P. A.; Schaefer III, H. F.; Schreiner, P. R., Eds.; John Wiley & Sons: Chichester, 1998; Vol. 3, 1827-1835.
    • (1998) In Encyclopedia of Computational Chemistry , vol.3 , pp. 1827-1835
    • Fleisher, U.1    Van Wüllen, C.2    Kutzelnigg, W.3
  • 28
    • 0342596423 scopus 로고    scopus 로고
    • (a) To make the discussion tractable, we and others (Ref. 22b) arbitrarily assign the convention that if a molecule has less than half the magnitude of NICS value in comparison to that of benzene, it is not aromatic
    • (a) To make the discussion tractable, we and others (Ref. 22b) arbitrarily assign the convention that if a molecule has less than half the magnitude of NICS value in comparison to that of benzene, it is not aromatic.
  • 30
    • 0343902162 scopus 로고    scopus 로고
    • The computed binding energy (MP2/6-311+G7z.ast;*) between the ammonium cation and squaramide is ΔE=-41.58 kcal/mol. We have compared it with the corresponding binding energy between the ammonium cation and a system where the increase in aromaticity is not possible, i.e. 3,4-diaminecyclobutane-1,2-dione, and the resulting binding energy is ΔE=-29.49 kcal/mol. This large difference might be attributed in part to the gain in aromaticity and in part to the higher basicity of the oxygen atoms in squaramide
    • The computed binding energy (MP2/6-311+G**) between the ammonium cation and squaramide is ΔE=-41.58 kcal/mol. We have compared it with the corresponding binding energy between the ammonium cation and a system where the increase in aromaticity is not possible, i.e. 3,4-diaminecyclobutane-1,2-dione, and the resulting binding energy is ΔE=-29.49 kcal/mol. This large difference might be attributed in part to the gain in aromaticity and in part to the higher basicity of the oxygen atoms in squaramide.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.