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Volumn 125, Issue 49, 2003, Pages 15110-15113

Heats of Formation of [2.2]Paracyclophane-1-ene and [2.2]Paracyclophane-1,9-diene - An Experimental Study

Author keywords

[No Author keywords available]

Indexed keywords

CALORIMETERS; ENTHALPY; SUBLIMATION; TRANSPIRATION; X RAY CRYSTALLOGRAPHY;

EID: 0344667433     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0374628     Document Type: Article
Times cited : (32)

References (56)
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    • (c) Bodwell, G. J. Angew. Chem. 1996, 108, 2221-2224; Angew. Chem., Int. Ed. Engl. 1996, 35, 2085-2088.
    • (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 2085-2088
  • 19
    • 0000220484 scopus 로고    scopus 로고
    • For the computational results concerning the geometry of [2.2]paracyclophane (1) at different levels of theory, see: (c) Henseler, D.; Hohlneicher, G. J. Phys. Chem. A 1998, 102, 10828-10833.
    • (1998) J. Phys. Chem. A , vol.102 , pp. 10828-10833
    • Henseler, D.1    Hohlneicher, G.2
  • 20
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    • The diene 3 reacts more rapidly with diazomethane/copper(I) chloride than 1. (a) Näder, R.; de Meijere, A. Angew. Chem. 1976, 88, 153-154; Angew. Chem., Int. Ed. Engl. 1976, 15, 166-167.
    • (1976) Angew. Chem. , vol.88 , pp. 153-154
    • Näder, R.1    De Meijere, A.2
  • 21
    • 84982474919 scopus 로고
    • The diene 3 reacts more rapidly with diazomethane/copper(I) chloride than 1. (a) Näder, R.; de Meijere, A. Angew. Chem. 1976, 88, 153-154; Angew. Chem., Int. Ed. Engl. 1976, 15, 166-167.
    • (1976) Angew. Chem., Int. Ed. Engl. , vol.15 , pp. 166-167
  • 22
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    • Under the conditions, under which 3 undergoes cycloaddition of singlet oxygen, 1 is completely inert: (b) Erden, I.; Gölitz, P.; Näder, R.; de Meijere, A. Angew. Chem. 1981, 93, 605-606; Angew. Chem., Int. Ed. Engl. 1981, 20, 583-585.
    • (1981) Angew. Chem. , vol.93 , pp. 605-606
    • Erden, I.1    Gölitz, P.2    Näder, R.3    De Meijere, A.4
  • 23
    • 84985616472 scopus 로고
    • Under the conditions, under which 3 undergoes cycloaddition of singlet oxygen, 1 is completely inert: (b) Erden, I.; Gölitz, P.; Näder, R.; de Meijere, A. Angew. Chem. 1981, 93, 605-606; Angew. Chem., Int. Ed. Engl. 1981, 20, 583-585.
    • (1981) Angew. Chem., Int. Ed. Engl. , vol.20 , pp. 583-585
  • 24
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    • Dissertation, Universität Hamburg
    • The [4+2] cycloaddition of N-phenyltriazolinedione (PTAD) to 3 proceeds at ambient temperature within 8 h, see: (c) Höfer, J. Dissertation, Universität Hamburg, 1989.
    • (1989)
    • Höfer, J.1
  • 25
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    • The [4+2] cycloaddition of PTAD to 1 requires 138 h at ambient temperature, see: (d) Kleinschroth, J.; Hopf, H. Angew. Chem. 1982, 94, 485-496; Angew. Chem., Int. Ed. Engl. 1982, 21, 469-480.
    • (1982) Angew. Chem. , vol.94 , pp. 485-496
    • Kleinschroth, J.1    Hopf, H.2
  • 26
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    • The [4+2] cycloaddition of PTAD to 1 requires 138 h at ambient temperature, see: (d) Kleinschroth, J.; Hopf, H. Angew. Chem. 1982, 94, 485-496; Angew. Chem., Int. Ed. Engl. 1982, 21, 469-480.
    • (1982) Angew. Chem., Int. Ed. Engl. , vol.21 , pp. 469-480
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    • note
    • -3. Crystallographic data (excluding structure factors) for the hydrocarbon 2 have been deposited as supplementary publication no. CCDC-215005 (measurement at 100 K) and CCDC-215006 (measurement at 293 K) with the Cambridge Crystallographic Data Centre. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (Fax: (+44)1223-336-033; E-mail: deposit@ccdc.cam.ac.uk).
  • 43
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    • note
    • The X-ray crystal structure of [2.2]paracyclophane-1,9-diene (3) was recently reinvestigated with higher precision at low temperature (133 K): Negru, M.; Jones, P. G.; Hopf, H., unpublished results. Cf.: Negru, M. Diplomarbeit, Technische Universität Braunschweig, 2003. The authors are grateful to Professor Dr. Henning Hopf, TU Braunschweig, Germany, for disclosing to us the atomic coordinates of 3, enabling us to calculate the values of angles α and β in 3.
  • 44
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    • note
    • For compounds 2 and 3, the values of angles α, α′, β, and β′ were calculated from atomic coordinates available elsewhere4d.21 or obtained in this work. The values of angles α and β for paracyclophane (1) were taken from its reinvestigated X-ray crystal structure analysis.4b However, these values differ significantly from those calculated by us for 1 using a set of atomic coordinates taken from an earlier crystallographic investigation4c (α = 14.1°, β = 7.2° at ambient temperature of α = 14.0®, β = 8.9° (at 93 K)).
  • 55
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.