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Volumn 62, Issue 9, 1997, Pages 2732-2737

The Elusive Antiaromaticity of Maleimides and Maleic Anhydride: Enthalpies of Formation of N-Methylmaleimide, N-Methylsuccinimide, N-Methylphthalimide, and N-Benzoyl-N-methylbenzamide

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EID: 0001074320     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9621985     Document Type: Article
Times cited : (51)

References (42)
  • 4
    • 1542577206 scopus 로고    scopus 로고
    • Ph.D. Thesis, University of Maryland Baltimore County
    • (b) Mumper, M. W., Ph.D. Thesis, University of Maryland Baltimore County, 1996.
    • (1996)
    • Mumper, M.W.1
  • 7
    • 0003958846 scopus 로고
    • John Wiley & Sons: New York
    • Garratt, P. J. Aromaticity; John Wiley & Sons: New York, 1986.
    • (1986) Aromaticity
    • Garratt, P.J.1
  • 9
    • 1542472596 scopus 로고    scopus 로고
    • note
    • This assignment arises from counting the π electrons as two from the carbon-carbon double bond and two from the nitrogen or oxygen as is done to arrive at an aromatic count to six electrons in pyrrole or furan, respectively. The two carbonyl groups are considered not to contribute electrons at all as done to arrive at six electrons for either 2- or 4-pyridone to be considered aromatic.
  • 10
    • 0003427206 scopus 로고
    • Thermochemical Research Center: College Station, TX
    • We accept the value of the enthalpy of formation of maleic anhydride from the literature, as well as that of many ancillary substances. Unless otherwise said, these and any other unreferenced data will be taken from the following archive: Pedley, J. B. Thermochemical Data of Organic Compounds, 3rd ed.; Thermochemical Research Center: College Station, TX, 1994.
    • (1994) Thermochemical Data of Organic Compounds, 3rd Ed.
    • Pedley, J.B.1
  • 11
    • 0003206784 scopus 로고
    • Presentation of combustion calorimetric data in the primary literature
    • Sunner, S., Mänsson, M., Eds.; Pergamon Press: Oxford, Chapter 7
    • (a) Westrum, E. F., Jr. Presentation of combustion calorimetric data in the primary literature. In Combustion Calorimetry; Sunner, S., Mänsson, M., Eds.; Pergamon Press: Oxford, 1979; Chapter 7.
    • (1979) Combustion Calorimetry
    • Westrum Jr., E.F.1
  • 12
    • 0003324453 scopus 로고
    • Assignment of uncertainties
    • Sunner, S., Mänsson, M., Eds.; Pergamon Press: Oxford, Chapter 6
    • (b) Olofsson, G. Assignment of uncertainties. In Combustion Calorimetry; Sunner, S., Mänsson, M., Eds.; Pergamon Press: Oxford, 1979; Chapter 6.
    • (1979) Combustion Calorimetry
    • Olofsson, G.1
  • 13
    • 0010093771 scopus 로고
    • Recommended key values for thermodynamics, 1975
    • CODATA. Recommended key values for thermodynamics, 1975. J. Chem. Thermodyn, 1976, 8, 603.
    • (1976) J. Chem. Thermodyn , vol.8 , pp. 603
  • 15
    • 85023030901 scopus 로고
    • These two results are from ref 5. Encouragingly, much the same difference is derivable from reactions of 1,3-diphenylbenzoisofuran with maleic anhydride and a whole series of variously substituted N- phenylmaleimides, cf.: Kiselev, V. D.; Ustyugov, A. N.; Breus, I. P.; Konovalov, A. I. Dokl. Chem. 1977, 234, 320.
    • (1977) Dokl. Chem. , vol.234 , pp. 320
    • Kiselev, V.D.1    Ustyugov, A.N.2    Breus, I.P.3    Konovalov, A.I.4
  • 17
    • 1542577198 scopus 로고    scopus 로고
    • note
    • This parallels customary assumptions as to the relatively greater aromatic stabilization of benzene over naphthalene and the relatively greater destabilization of p-benzoquinone over 1,4-naphthoquinone.
  • 18
    • 0003825877 scopus 로고
    • Keehn, P. M., Rosenfeld, S. M., Eds.; Academic Press: New York
    • See, for example, the use of this regularity in the following: Liebman, J. F. The Cyclophanes; Keehn, P. M., Rosenfeld, S. M., Eds.; Academic Press: New York, 1983.
    • (1983) The Cyclophanes
    • Liebman, J.F.1
  • 20
    • 0000745425 scopus 로고
    • -1) discussed in the following: Cox, J. D.; Pilcher, G. Thermochemistry of Organic and Organometallic Compounds; Academic Press: New York, 1970.
    • (1951) J. Am. Chem. Soc. , vol.73 , pp. 4766
    • Serijan, K.T.1    Wise, P.H.2
  • 30
    • 0002120842 scopus 로고
    • (iv) Indium and tin: standard material and melting point supplied by Perkin-Elmer
    • (b) The DSC calibration data was obtained from (i) n-octadecane: NPL Certificate of Measurement CRM No M 14-11, Set of Ten Melting point Standards, National Physical Laboratory, Teddington, 1980. (ii) n-octadecanoic acid: Lopez de la Fuente F. L. Ph.D. Thesis, Facultad de Ciencias Químicas, Universidad Complutense, Madrid, 1989. (iii) Benzoic acid: Serge, S.; Cammerga, H. K. Thermochim. Acta 1985, 94, 17-31. (iv) Indium and tin: standard material and melting point supplied by Perkin-Elmer.
    • (1985) Thermochim. Acta , vol.94 , pp. 17-31
    • Serge, S.1    Cammerga, H.K.2


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