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1,3-INTERACTION BETWEEN AMIDE NITROGENS------Possibility and Limitation

Research Project

Project/Area Number 02640384
Research Category

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

Allocation TypeSingle-year Grants
Research Field 有機化学一般
Research InstitutionTHE UNIVERSITY OF TOKYO

Principal Investigator

TAKEUCHI Yoshito  Department of Chemistry, College of Arts & Sciences, The University of Tokyo, Professor, 教養学部, 教授 (80012384)

Co-Investigator(Kenkyū-buntansha) YOSHIMURA Shin  Department of Chemistry, College of Arts & Sciences, The University of Tokyo, As, 教養学部, 助手 (20182818)
OGAWA Keiichiro  Department of Chemistry, College of Arts & Sciences, The University of Tokyo, As, 教養学部, 助教授 (50114426)
Project Period (FY) 1990 – 1992
Project Status Completed (Fiscal Year 1992)
Budget Amount *help
¥2,100,000 (Direct Cost: ¥2,100,000)
Fiscal Year 1992: ¥400,000 (Direct Cost: ¥400,000)
Fiscal Year 1991: ¥800,000 (Direct Cost: ¥800,000)
Fiscal Year 1990: ¥900,000 (Direct Cost: ¥900,000)
KeywordsAmide-type nitrogen / 1,3-Interaction / Amine-type nitrogen / Variable temperature NMR / X-ray crystallographic analysis / Restricted rotation of amides / Nitrogen inversion / 動物NMR / 環の反転障壁 / ヘテラピペリジンの反転 / ピペリジンの反転 / ヘテラインドリジジン / MNDO法 / ヘテラキノリジジン / ダイナミックNMR / アミドの平面性 / 束縛回転 / NMR / ベンズアミド / 回転障壁 / 反転 / エネルギ-障壁
Research Abstract

The purpose of this investigation is to explore the possible 1,3- interaction between amide-type nitrogen atoms. It seems that 1,3,5- tribenzoylperhydro-1,3,5-triazine(A) is the most appropriate system for this purpose.
The X-ray crystallographic analysis of (A) revealed that the molecule is symmetric and the nitrogen atoms have approximate trigonal structures. This means that the nitrogen involved is a conventional amide nitrogen, which is in contrast to the tetrahedral nitrogen in 1,2-diacylhydrazine. The results were already published in Acta Cryst.
Though no indication of 1,3-interaction between amide nitrogens, we explored variable temperature of C-13 NMR spectra of (A). As the temperature lowered, there was observed a change of line-shape which corresponds to the amide rotation. As the temperature further lowered, there was observed the second chemical exchange. This rate process is most likely due to the nitrogen inversion. Unfortunately the NMR spectrometer in general cannot reach temperature below-100C and hence we failed to finalize our interpretation.
In conclusion, it is likely that in (A) the nitrogen atoms have a tetrahedral character to some extent. This might mean that the 1,3-interaction between amide nitrogens do exist. Further study would be required to finalize this conclusion.;C and hence we failed to finalize our interpretation.

Report

(4 results)
  • 1992 Annual Research Report   Final Research Report Summary
  • 1991 Annual Research Report
  • 1990 Annual Research Report
  • Research Products

    (9 results)

All Other

All Publications (9 results)

  • [Publications] K.OGAWA,S.YOSHIMURA,Y.TAKEUCHI et al.: "Structure of 1、3、5-Tribenzoylperhydro-1、3、5-triazine" Acta Crystallographca. C48. 1071-1074 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Yoshito Takeuchi: "Nclear Magnetic Resonance Methods, in “Cyclic Organonitrtgen Stereodynamics",ed by Yoshito Takeuchi and Joseph B. Lambert'" VCH(New York,USA), 9-30 (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Keiichiro Ogawa, S. Yoshimura, Yoshito Takeuchi, A. Katritizky, and Ramia Murugan: "Structure of 1,3,5-Tribenzoyl-1,3,5-triazine" Acta Crystallographica. C48. 1071-1074 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Yoshito Takeuch: "Nuclear Magnetic Resonance Methods" [Cyclic Organonitrogen Stereodynamics], ed. by Joseph B. Lambert and Yoshito Takeuchi, VCH, New York. 9-30 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] K.Ogawa,S.Yoshimura,Y,Takeuchi et al.: "Structure of 1,3,5ーTribenzoylperhydroー1,3,5ーtriazine" Acta Crystallographica. C48. 1071-1074 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] K.ogawa,S.Yoshimura,Y.Takeuchi,A.Katritzky,R.Murgen: "Structure of 1,3,5ーTribenzoylperhydroー1,3,5ーtriazine" Acta Crystallographica. (1992)

    • Related Report
      1991 Annual Research Report
  • [Publications] J.B.Lambert and Y.Takeuchi(ed.),Y.Takeuchi: "Cyclic Organonitrogen Stereodynamics“Nuclear Magnetic Resonance Methods"" VCH, 21 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] K.OGAWA: "Structure of 1,3,5ーTribenzoylperbydroー1,3,5ーtriazine" Acta Cryst.C.

    • Related Report
      1990 Annual Research Report
  • [Publications] J.B.Lambert&Y.TaKeuchi,eds.: "Stereodynamics of Organonitrogen Molecules" VCH, (1991)

    • Related Report
      1990 Annual Research Report

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Published: 1990-04-01   Modified: 2016-04-21  

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