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The CH/pi Interaction and Related Interactions between Hydrocarbon Groups.

Research Project

Project/Area Number 61430009
Research Category

Grant-in-Aid for General Scientific Research (A)

Allocation TypeSingle-year Grants
Research Field 有機化学一般
Research InstitutionYokohama National University

Principal Investigator

HIROTA Minoru  Faculty of Engineering, Yokohama National University, 工学部, 教授 (00017881)

Co-Investigator(Kenkyū-buntansha) SUEZAWA Hiroko  Faculty of Engineering, Yokohama National University, 工学部, 教務職員 (30251771)
SAKAKIBARA Kazuhisa  Faculty of Engineering, Yokohama National University, 工学部, 助手 (80114966)
Project Period (FY) 1986 – 1987
Project Status Completed (Fiscal Year 1987)
Budget Amount *help
¥10,000,000 (Direct Cost: ¥10,000,000)
Fiscal Year 1987: ¥1,000,000 (Direct Cost: ¥1,000,000)
Fiscal Year 1986: ¥9,000,000 (Direct Cost: ¥9,000,000)
KeywordsThe CH / pi interaction / molecular interaction / CH hydrogen bonding / hydrophobic interaction / 疎水基間相互作用 / アルキル芳香族化合物 / 水素結合類似の相互作用 / 立体配座解折 / 置換基効果
Research Abstract

Experimental evidence in favor of the presence of the attractive interaction between alkyl and pi-electron bearing groups has been accumulated in recent decades. This reseach project started in the aim of elucidating the nature of this sort of interaction and estimating the energy of interaction.
Infrared spectra of a series of isopropyl-2-d (p-substituted Phenyl)-ethyl ketones showed two absorption bands assignable to the free and the CH/pi interacted conformers. The substituent effect on the equilibrium constants and the enthalpy difference between the two conformers determined by infrared spectroscopy were in line with the interpretation that the interaction is hydrogen-bond-like; revealing the fact that the interaction is more favorable when the substituent becomes more electron-donating. Similar results were obtained in the case of intermolecular CH/pi interaction between substituted benzenes and chloroform.
Semi-empirical and ab initio MO calculations on the CH/pi interacted system showed that there is a non-zero overlap between the C-H and the carbon atom bearing pi-electrons. This might be other evidence for the hydrogen-bond-like character of the CH/pi interaction. In contrast, molecular force field calculation on the interacted conformation indicated the important contribution of the dispersive force to its stabilization. In conclusion, the CH/pi interaction is a weak hydrogen bonding in which the dispersive interaction plays a relatively important role.

Report

(2 results)
  • 1987 Final Research Report Summary
  • 1986 Annual Research Report
  • Research Products

    (24 results)

All Other

All Publications (24 results)

  • [Publications] 末沢 裕子: Bull. Chem. Soc. Jpn.59. 2362-2364 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] 安部 和久: Bull. Chem. Soc. Jpn.59. 3125-3130 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] 唐津 誠: Bull. Chem. Soc. Jpn.59. 3529-3534 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] 里中 初: Bull. Chem. Soc. Jpn.60. 953-961 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] J. Edgar Anderson: J. Chem. Soc. Chem. Commun.1987. 554-555 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] 末沢 裕子: Bull. Chem. Soc. Jpn.60. 3973-3978 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] 室伏 克己: J. Chem. Soc. Perkin Trans. 2. 1987. 1829-1833 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] 里中 初: Bull. Chem. Soc. Jpn.

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] 西尾 元宏: Tetrahedron.

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] 広田 穣: Bull. Chem. Soc. Jpn.

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Hiroko Suezawa, Minoru Hirota, Yasuhiro Shibata, Isao Takeuchi, and Yoshiki Hamada: "NMR Spectra of Dimethyl 1-Acetyl-1,2-dihydro-2quinolylphosphonate and Related Compounds." Bull. Chem. Soc. Jpn.59. 2362-2364 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Kazuhisa Abe, Kohichi Ito, Hiroko Suezawa, Minoru Hirota, and Motohiro Nishio: "Conformational Study of Acyclic Alcohols by NMR Spectroscopic Analysis,Molecular Force Field and Ab Initio Calculations." Bull. Chem. Soc. Jpn.59. 3125-3130 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Makoto Karatsu, Hiroko Suezawa, Kazuhisa Abe, Minoru Hirota, and Motohiro Nishio: "Infrared C-D Strtetching and H-NMR Spectra of Isopropyl-2d 1-(p-Substituted Phenyl)ethyl Ketones. Evidence for the Hydrogen-Bond-Like C-D/<p:> Interaction." Bull. Chem. Soc. Jpn.59. 3529-3534 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Hajime Satonaka, Kazuhisa Abe, and Minoru Hirota: "^<13>C NMR Spectra of Substituted 2-Thiophenecarboxylic Acid Methyl Esters and MNDO Calculations." Bull. Chem. Soc. Jpn.60. 953-961 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] J. Edgar Anderson, Katsuhiko Heki, and Minoru Hirota: "Setting the Anomeric Effect against Steric Effects in Simple Acyclic Acetals. Non-anomeric Non-classical Conformations. An NMR Investigation." J. Chem. Soc. Chem. Commun.1987. 554-555 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Hiroko Suezawa, Kin-ya Tsuchiya, Eiji Tahara, and Minoru Hirota: "The Effect of Intramolecular Hydrogen Bonding on the Rotational Barrier about the C-N Bonds of o-Hydroxyarenecarboxamides." Bull. Chem. Soc. Jpn.60. 3973-3978 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Katsumi Murofushi, Kazuhisa Abe, and Minoru Hirota: "Substituent Effect on the Spin-trapping Reactions of Substituted N-Benzylidene-t-butylamine N-Oxides." J. Chem. Soc. Perkin Trans. 2. 1987. 1829-1833 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Hajime Satonaka, Kazuhisa Abe, and Minoru Hirota: "NMR Specroscopic Study of the Conformational Preference of Methoxy-carbonyl and Methyl Substituted Thiophenecarbaldehydes." Bull. Chem. Soc. Jpn.61. (1988)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Motohiro Nishio and Minoru Hirota: "The CH/<pi> Interaction. Implication in Organic Chemistry." Tetrahedron. 44. (1988)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Minoru Hirota, Akemi Yokoo, Masaki Tsushima, Hiroko Suezawa: "Substituent Effect on the CH/<pi> Interacted Complex Formation." Bull. Chem. Soc. Jpn.61. (1988)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] 安部和久: Bull.Chem.Soc.Jpn.59. 3125-3130 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] 唐津誠: Bull.Chem.Soc.Jpn.59. 3529-3534 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] 里中初: Bull.Chem.Soc.Jpn.603月号. (1987)

    • Related Report
      1986 Annual Research Report
  • [Publications] 室伏克己: J.Chem.Soc.Perkin II. (1987)

    • Related Report
      1986 Annual Research Report

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Published: 1987-03-31   Modified: 2016-04-21  

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