The molecular structure of thiazole, determined by the combined analysis of gas-phase electron diffraction (GED) data and rotational constants and by ab initio calculations

Bone, Simon F.; Smart, Bruce A.; Gierens, Hedi; Morrison, Carole A.; Brain, Paul T.; Rankin, David W. H.

doi:10.1039/a809867k

Cited by 13 publications

(5 citation statements)

References 8 publications

(8 reference statements)

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“…In 1971, the structure of this molecule was determined by Nygaard et al [5] from additional microwave investigations of several isotopomers. More recently (1999) this structure was slightly modified by Bone et al [6] by combination of their electron diffraction data with the microwave data [4,5].…”

Section: Introductionmentioning

confidence: 97%

The vibrational spectrum of thiazole between 600 and 1400cm−1 revisited: A combined high-resolution infrared and theoretical study

Hegelund¹,

Larsen²,

Palmer³

2007

Journal of Molecular Spectroscopy

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Section: Introductionmentioning

confidence: 97%

The vibrational spectrum of thiazole between 600 and 1400cm−1 revisited: A combined high-resolution infrared and theoretical study

Hegelund¹,

Larsen²,

Palmer³

2007

Journal of Molecular Spectroscopy

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“…2 has C S symmetry. An electron diffraction (ED) study [21] has also been reported. Molecular properties from these MW studies, such as dipole moments [17], 14 N quadrupole coupling constants [18], and nonlocal contributions of the diamagnetic susceptibility component perpendicular to the ring [19], are known from these MW studies.…”

Section: Molecular Structurementioning

confidence: 95%

The electronic states of thiazole studied by VUV absorption spectroscopy and ab initio configuration interaction methods

Palmer

2008

Chemical Physics

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The thiazole VUV absorption spectrum over the range 5-12 eV shows intense bands near 5.4, 6.0, 7-7.8, 8.2-8.8, 9.2-10.1 and 10.2-11.0 eV; there is marked vibrational structure in the 7.5-8.5 and 10.2-11 eV regions. A number of Rydberg states have been identified, largely from IE 1 , but also tentative values for ones from IE 2 and IE 4 . Electronic excitation energies for valence and Rydberg-type states have been computed using ab initio multi-reference multi-root CI methods, and these have been compared with the VUV envelope. Calculated energies for low-lying Rydberg states are close to those expected, and there is generally a good correlation between the theoretical intensities and calculated density of states, with the experimental envelope. The CI studies used a triple zeta + polarization basis set, augmented by diffuse (Rydberg) orbitals. The lowest absorption bands are dominated by intense pp * (A 0 ) valence states, together with LP N p * and pr * states, which are relatively weak. The lowest Rydberg states arise from excitation of the occupied MOs in the sequential order p 4 < r 18 (LP N ) < p 3 < p 2 < r 17 (LP S ) this same order is determined by CI for ionisation in the UV-PES spectrum. Adiabatic structures of the r-and p-triplets, -cations and the p-anion have been compared with the ground state structure. The known phosphorescence of thiazole is from the 3 A triplet state (C 1 symmetry) where significant twisting of C 5 H and S to opposite sides of the mean plane occurs. Some theoretical molecular properties of thiazole are described, which give good agreement with microwave spectral data.

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“…Of interest for comparison with (II) are the high-precision structural data for the molecular structure of thiazole (IV) from a combined analysis of gas-phase electron diffraction data, rotational constants and ab initio calculations (Bone et al, 1999). The corresponding mean values for (II) are SÐ C(C) = 1.713 (2) A Ê , SÐC(N) = 1.730 (6) A Ê , CÐN = 1.391 (2) A Ê and C N = 1.299 (2) A Ê , demonstrating that the thiazole groups are relatively unperturbed through molecular or crystal packing forces in (II) and are comparable to the gasphase structure data for (IV).…”

Section: Commentmentioning

confidence: 99%

Methyl 2-(4-ferrocenylbenzamido)thiophene-3-carboxylate and ethyl 2-(4-ferrocenylbenzamido)-1,3-thiazole-4-acetate, a unique ferrocene derivative containing a thiazole moiety

Alley¹,

Gallagher²,

Hooper³

et al. 2005

Acta Crystallogr C

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The conformations and hydrogen bonding in the thiophene and thiazole title compounds, [Fe(C5H5)(C20H14NO3S)], (I), and [Fe(C5H5)(C19H17N2O3S)], (II), are discussed. The sequence (C5H4)-(C6H4)-(CONH)-(C4H2S)-(CO2Me) of rings and moieties in (I) is close to being planar; all consecutive interplanar angles are less than 10 degrees . An intramolecular N-H...O=C(ester) hydrogen bond [graph set S6, N...O = 2.768 (2) A and N-H...O = 134 (2) degrees ] effects the molecular planarity, and aggregation occurs via hydrogen-bonded chains formed from intermolecular C(ar)-H...O=C(ester/amide) interactions along [010], with C...O distances ranging from 3.401 (3) to 3.577 (2) A. The thiazole system in (II) crystallizes with two molecules in the asymmetric unit; these differ in the conformation along their long molecular axes; for example, the interplanar angle between the phenylene (C6H4) and thiazole (C3NS) rings is 8.1 (2) degrees in one molecule and 27.66 (14) degrees in the other. Intermolecular N-H...O=C(ester) hydrogen bonds [N...O = 2.972 (4) and 2.971 (3) A], each augmented by a C(phenylene)-H...O=C(ester) interaction [3.184 (5) and 3.395 (4) A], form motifs with graph set R2(1)(7) and generate chains along [100]. The amide C=O groups do not participate in hydrogen bonding. Compound (II) is the first reported ferrocenyl-containing thiazole structure.

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The molecular structure of thiazole, determined by the combined analysis of gas-phase electron diffraction (GED) data and rotational constants and by ab initio calculations

Cited by 13 publications

References 8 publications

The vibrational spectrum of thiazole between 600 and 1400cm−1 revisited: A combined high-resolution infrared and theoretical study

The vibrational spectrum of thiazole between 600 and 1400cm−1 revisited: A combined high-resolution infrared and theoretical study

The electronic states of thiazole studied by VUV absorption spectroscopy and ab initio configuration interaction methods

Methyl 2-(4-ferrocenylbenzamido)thiophene-3-carboxylate and ethyl 2-(4-ferrocenylbenzamido)-1,3-thiazole-4-acetate, a unique ferrocene derivative containing a thiazole moiety

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