Conformational stability of bicyclo[3.3.1]nonane-2,6-dione and bicyclo[3.3.1]nonane-2,9-dione: Ab initio calculations and vibrational spectroscopy studies

A. Alkauskas, J. Ceponkus, B. Mikulskiene, V. Aleksa, E. Butkus, V. Sablinskas

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

The conformational stability of newly synthesised bicyclo[3.3.1]nonane-2,6-dione C9H12O2 (D26) and bicyclo[3.3.1]nonane-2,9-dione C9H12O2 (D29) was studied. Ab initio calculations (HF level using 6-31G** basis set) reveal that due to six-membered ring inversion four conformers exist in the case of D26, whereas five of them exist for D29. The double-chair (CC) conformer is the most stable for D26 and the chair-boat (CB) conformer is 3.4 kJ mol-1 higher in energy. On the contrary, the chair-boat (CBo) conformer of D29 is the most stable and the chair-chair conformer (CC) is 2.5 kJ mol-1 higher in energy. Raman and IR spectra of the title compounds were recorded in solid, liquid and gas phases for the first time. Assignment of vibrational spectral bands for both molecules was made by comparing theoretical and experimental spectra.

Original languageEnglish
Pages (from-to)517-521
Number of pages5
JournalJournal of Molecular Structure
Volume563-564
DOIs
Publication statusPublished - May 28 2001
Externally publishedYes

Fingerprint

nonanes
Vibrational spectroscopy
Ships
Boats
Dione
seats
Spectrum Analysis
spectroscopy
Gases
boats
Molecules
Liquids
spectral bands
bicyclo(3.3.1)nonane
solid phases
liquid phases
inversions
Raman spectra
vapor phases
energy

Keywords

  • Bicyclo[3.3.1]-2,9-dione
  • Bicyclo[3.3.1]nonane-2,6-dione
  • Conformational stability
  • Vibrational spectroscopy

ASJC Scopus subject areas

  • Structural Biology
  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Spectroscopy
  • Atomic and Molecular Physics, and Optics

Cite this

Conformational stability of bicyclo[3.3.1]nonane-2,6-dione and bicyclo[3.3.1]nonane-2,9-dione : Ab initio calculations and vibrational spectroscopy studies. / Alkauskas, A.; Ceponkus, J.; Mikulskiene, B.; Aleksa, V.; Butkus, E.; Sablinskas, V.

In: Journal of Molecular Structure, Vol. 563-564, 28.05.2001, p. 517-521.

Research output: Contribution to journalArticle

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abstract = "The conformational stability of newly synthesised bicyclo[3.3.1]nonane-2,6-dione C9H12O2 (D26) and bicyclo[3.3.1]nonane-2,9-dione C9H12O2 (D29) was studied. Ab initio calculations (HF level using 6-31G** basis set) reveal that due to six-membered ring inversion four conformers exist in the case of D26, whereas five of them exist for D29. The double-chair (CC) conformer is the most stable for D26 and the chair-boat (CB) conformer is 3.4 kJ mol-1 higher in energy. On the contrary, the chair-boat (CBo) conformer of D29 is the most stable and the chair-chair conformer (CC) is 2.5 kJ mol-1 higher in energy. Raman and IR spectra of the title compounds were recorded in solid, liquid and gas phases for the first time. Assignment of vibrational spectral bands for both molecules was made by comparing theoretical and experimental spectra.",
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T2 - Ab initio calculations and vibrational spectroscopy studies

AU - Alkauskas, A.

AU - Ceponkus, J.

AU - Mikulskiene, B.

AU - Aleksa, V.

AU - Butkus, E.

AU - Sablinskas, V.

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N2 - The conformational stability of newly synthesised bicyclo[3.3.1]nonane-2,6-dione C9H12O2 (D26) and bicyclo[3.3.1]nonane-2,9-dione C9H12O2 (D29) was studied. Ab initio calculations (HF level using 6-31G** basis set) reveal that due to six-membered ring inversion four conformers exist in the case of D26, whereas five of them exist for D29. The double-chair (CC) conformer is the most stable for D26 and the chair-boat (CB) conformer is 3.4 kJ mol-1 higher in energy. On the contrary, the chair-boat (CBo) conformer of D29 is the most stable and the chair-chair conformer (CC) is 2.5 kJ mol-1 higher in energy. Raman and IR spectra of the title compounds were recorded in solid, liquid and gas phases for the first time. Assignment of vibrational spectral bands for both molecules was made by comparing theoretical and experimental spectra.

AB - The conformational stability of newly synthesised bicyclo[3.3.1]nonane-2,6-dione C9H12O2 (D26) and bicyclo[3.3.1]nonane-2,9-dione C9H12O2 (D29) was studied. Ab initio calculations (HF level using 6-31G** basis set) reveal that due to six-membered ring inversion four conformers exist in the case of D26, whereas five of them exist for D29. The double-chair (CC) conformer is the most stable for D26 and the chair-boat (CB) conformer is 3.4 kJ mol-1 higher in energy. On the contrary, the chair-boat (CBo) conformer of D29 is the most stable and the chair-chair conformer (CC) is 2.5 kJ mol-1 higher in energy. Raman and IR spectra of the title compounds were recorded in solid, liquid and gas phases for the first time. Assignment of vibrational spectral bands for both molecules was made by comparing theoretical and experimental spectra.

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