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Volumn 1, Issue 7, 2003, Pages 1240-1249

Carboxylic acid clathrate hosts of Diels-Alder adducts of phencyclone and 2-alkenoic acids. Role of bidentate C-H ⋯ O hydrogen bonds between the phenanthrene and carbonyl groups in host-host networks

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; ALCOHOLS; CALCULATIONS; HYDROGEN BONDS; INCLUSIONS; KETONES; MOLECULES; SYNTHESIS (CHEMICAL); THERMOANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 0141975257     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b212129h     Document Type: Article
Times cited : (15)

References (42)
  • 27
    • 84988746109 scopus 로고    scopus 로고
    • note
    • Although the crystal structure of 3ac·dioxane (1:1) shows that two dioxane molecules are located at the different positions, the DATA spectrum did not show two endothermic peaks but a single peak at 155°C.
  • 28
    • 0003497132 scopus 로고
    • benjamin, New York
    • (a) The intermolecular hydrogen-bond distance (OH ⋯ O) between carboxylic acids is 2.59 Å: W. C. Hamilton and J. A. Ibers, Hydrogen Bonding in Solids, benjamin, New York, 1968
    • (1968) Hydrogen Bonding in Solids
    • Hamilton, W.C.1    Ibers, J.A.2
  • 29
    • 84988744858 scopus 로고    scopus 로고
    • note
    • 9distances are unreliable. The AM1 and PM5 distances (C=O ⋯ O) are 3.070 Å and 3.43 Å, respectively, longer than the experimental and PM3 values. The heats of reaction for the 2:1 complex formation are 6.43, 8.87 and 6.301 kcal/mol for AM1, PM3 and PM5, respectively.
  • 35
    • 84988740414 scopus 로고    scopus 로고
    • note
    • (a) AM1 and PM3 calculations were performed using MOPAC ver. 6.0 (QCPE No. 445) and MOPAC97, Fujitsu Ltd, Tokyo, Japan, 1998. PM5 calculations were performed using WinMOPAC V3.5, Fujitsu Ltd. Tokyo, Japan, 2002.
  • 36
    • 84988740332 scopus 로고    scopus 로고
    • note
    • The calculation data are available in our website (http://.yakko.pharm.kumamoto-u.ac.jp/).
  • 37
    • 84988791333 scopus 로고    scopus 로고
    • note
    • The partial structures of the interactions extracted from the crystal structures of the complexes were roughly reproduced by PM5 calculations. The PM3 calculation seems to overestimate the interaction energies.
  • 38
    • 84988740342 scopus 로고    scopus 로고
    • note
    • The HF/6-31G*, HF/6-31+G** and B3LYP/6-31+G* calculations on a model bidentate C-H ⋯ O interaction between acetone and phenanthrene (4,5-hydrogens) are 2.37, 2.10 and 1.89 kcal/mol, respectively (see ESI-7).
  • 39
    • 84988744808 scopus 로고    scopus 로고
    • note
    • The X-ray analysis showed that the guest was located at region A and the DSC analysis exhibited an endothermic peak at 110°C, lower than the bp (138°C).
  • 42
    • 84988740348 scopus 로고
    • ORTEP ORNL-3794. Oak Ridge National Laboratory, Tennessee, U. S. A.
    • C. K. Johnson, ORTEP ORNL-3794. Oak Ridge National Laboratory, Tennessee, U. S. A., 1965.
    • (1965)
    • Johnson, C.K.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.