Structural study of methyl isonicotinate by gas phase electron diffraction combined with ab initio calculations

Hajime Kiyono, Nobuhiko Kuze, Hideo Fujiwara, Hiroshi Takeuchi, Toru Egawa, Shigehiro Konaka

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

The molecular structure of methyl isonicotinate was studied by gas phase electron diffraction combined with ab initio calculations. The molecular skeleton was assumed to be planar. The determined values of principal structure parameters (rg and ∠α) are as follows: r(N-C) = 1.343(5) Å, r(C=C)ring = 1.401(3) Å, r(Cγ-C) = 1.499(9) Å, r(C=O) = 1.205(5) A. r(C(=O)- O) = 1.331(8) Å, r(O-CMe) = 1.430(8) Å, (r(C-H) = 1.103(10) Å, ∠CNC = 117.6(9)°, ∠CβCγCβ = 118.7(9)°, ∠Cβ,transCγ-C(=O) = 118.6(12), ∠CγO = 121.4(12)°, ∠CγC-O = 114.2(10)°, ∠COC = 115.4(15)°, where angled brackets denote average values and Cβ,transC denotes the carbon atom which is trans to the carbonyl oxygen atom. Values in parentheses are the estimated limits of error (3σ) referring to the last significant digit. The structure of the ring in methyl isonicotinate agrees with that of pyridine within experimental error. In contrast, the structure parameters of the COOCH3 group are significantly different from those of methyl acrylate and methyl acetate. These differences have been discussed in terms of hyperconjugation and steric effects.

Original languageEnglish
Pages (from-to)145-150
Number of pages6
JournalJournal of Molecular Structure
Volume376
Issue number1-3
Publication statusPublished - 1996
Externally publishedYes

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Electron diffraction
electron diffraction
Gases
vapor phases
Atoms
digits
rings
Carbon Monoxide
brackets
acrylates
musculoskeletal system
Molecular structure
acetates
oxygen atoms
pyridines
molecular structure
Carbon
Oxygen
carbon
atoms

ASJC Scopus subject areas

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

Cite this

Structural study of methyl isonicotinate by gas phase electron diffraction combined with ab initio calculations. / Kiyono, Hajime; Kuze, Nobuhiko; Fujiwara, Hideo; Takeuchi, Hiroshi; Egawa, Toru; Konaka, Shigehiro.

In: Journal of Molecular Structure, Vol. 376, No. 1-3, 1996, p. 145-150.

Research output: Contribution to journalArticle

Kiyono, H, Kuze, N, Fujiwara, H, Takeuchi, H, Egawa, T & Konaka, S 1996, 'Structural study of methyl isonicotinate by gas phase electron diffraction combined with ab initio calculations', Journal of Molecular Structure, vol. 376, no. 1-3, pp. 145-150.
Kiyono, Hajime ; Kuze, Nobuhiko ; Fujiwara, Hideo ; Takeuchi, Hiroshi ; Egawa, Toru ; Konaka, Shigehiro. / Structural study of methyl isonicotinate by gas phase electron diffraction combined with ab initio calculations. In: Journal of Molecular Structure. 1996 ; Vol. 376, No. 1-3. pp. 145-150.
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abstract = "The molecular structure of methyl isonicotinate was studied by gas phase electron diffraction combined with ab initio calculations. The molecular skeleton was assumed to be planar. The determined values of principal structure parameters (rg and ∠α) are as follows: r(N-C) = 1.343(5) {\AA}, r(C=C)ring = 1.401(3) {\AA}, r(Cγ-C) = 1.499(9) {\AA}, r(C=O) = 1.205(5) A. r(C(=O)- O) = 1.331(8) {\AA}, r(O-CMe) = 1.430(8) {\AA}, (r(C-H) = 1.103(10) {\AA}, ∠CNC = 117.6(9)°, ∠CβCγCβ = 118.7(9)°, ∠Cβ,transCγ-C(=O) = 118.6(12), ∠CγO = 121.4(12)°, ∠CγC-O = 114.2(10)°, ∠COC = 115.4(15)°, where angled brackets denote average values and Cβ,transC denotes the carbon atom which is trans to the carbonyl oxygen atom. Values in parentheses are the estimated limits of error (3σ) referring to the last significant digit. The structure of the ring in methyl isonicotinate agrees with that of pyridine within experimental error. In contrast, the structure parameters of the COOCH3 group are significantly different from those of methyl acrylate and methyl acetate. These differences have been discussed in terms of hyperconjugation and steric effects.",
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AU - Kiyono, Hajime

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N2 - The molecular structure of methyl isonicotinate was studied by gas phase electron diffraction combined with ab initio calculations. The molecular skeleton was assumed to be planar. The determined values of principal structure parameters (rg and ∠α) are as follows: r(N-C) = 1.343(5) Å, r(C=C)ring = 1.401(3) Å, r(Cγ-C) = 1.499(9) Å, r(C=O) = 1.205(5) A. r(C(=O)- O) = 1.331(8) Å, r(O-CMe) = 1.430(8) Å, (r(C-H) = 1.103(10) Å, ∠CNC = 117.6(9)°, ∠CβCγCβ = 118.7(9)°, ∠Cβ,transCγ-C(=O) = 118.6(12), ∠CγO = 121.4(12)°, ∠CγC-O = 114.2(10)°, ∠COC = 115.4(15)°, where angled brackets denote average values and Cβ,transC denotes the carbon atom which is trans to the carbonyl oxygen atom. Values in parentheses are the estimated limits of error (3σ) referring to the last significant digit. The structure of the ring in methyl isonicotinate agrees with that of pyridine within experimental error. In contrast, the structure parameters of the COOCH3 group are significantly different from those of methyl acrylate and methyl acetate. These differences have been discussed in terms of hyperconjugation and steric effects.

AB - The molecular structure of methyl isonicotinate was studied by gas phase electron diffraction combined with ab initio calculations. The molecular skeleton was assumed to be planar. The determined values of principal structure parameters (rg and ∠α) are as follows: r(N-C) = 1.343(5) Å, r(C=C)ring = 1.401(3) Å, r(Cγ-C) = 1.499(9) Å, r(C=O) = 1.205(5) A. r(C(=O)- O) = 1.331(8) Å, r(O-CMe) = 1.430(8) Å, (r(C-H) = 1.103(10) Å, ∠CNC = 117.6(9)°, ∠CβCγCβ = 118.7(9)°, ∠Cβ,transCγ-C(=O) = 118.6(12), ∠CγO = 121.4(12)°, ∠CγC-O = 114.2(10)°, ∠COC = 115.4(15)°, where angled brackets denote average values and Cβ,transC denotes the carbon atom which is trans to the carbonyl oxygen atom. Values in parentheses are the estimated limits of error (3σ) referring to the last significant digit. The structure of the ring in methyl isonicotinate agrees with that of pyridine within experimental error. In contrast, the structure parameters of the COOCH3 group are significantly different from those of methyl acrylate and methyl acetate. These differences have been discussed in terms of hyperconjugation and steric effects.

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