Tautomerization of formamide, 2-pyridone, and 4-pyridone: an ab initio study

Schlegel, H. Bernhard; Gund, Peter; Fluder, Eugene M.

doi:10.1021/ja00384a017

Cited by 200 publications

(113 citation statements)

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“…These distances are significantly shorter than those o b s e~e d (1.410(10) (24), 1.373(4) (25), and 1.400(5) A (26)) and calculated (1.408 A (27) and 1.390 A (28)) for 2-pyridones; slightly longer than those found (1.341 (3) (29) (26), and 1.250(7) A (3 1)) and calculated (1.264 (27) and 1.221 A (28)) for 2-pyridones; slightly shorter than those observed (1.321(3) (29) and 1.330(5) A (25)) and calculated (1.358 A (28)) for 2-hydroxypyridines; and equal witbin experimental error to that observed i n 10 (26) (1.317(7) A). The N-O(1) distance of 1.389(3) A in 6b is longer than the mean N-0 distance of 1.…”

Section: Resultsmentioning

confidence: 53%

Structural studies of organoboron compounds. XVIII. Crystal and molecular structures of 2,2-diphenyl-1,3-dioxa-3a-azonia-2-borataindan and 4-cyclohexyl-6-methyl-2,2-diphenyl-1,3-dioxa-3a-azonia-2-borataindan

Kliegel¹,

Nanninga²,

Rettig³

et al. 1983

Can. J. Chem.

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. 61, 2493 (1983). The crystal structures of 2,2-d1phenyl-l,3-dioxa-3a-azonia-2-borataindan, 6a, and 4-cyclohexyl-6-methyl-2,2-d~phenyl-1,3-dioxa-3a-azonia-2-borataindan, 6b, reported here represent the first crystallographic examples of coordination complexes of the anionic ligand derivedo from 2-hydroxypyridine N-oxide. Crystals of 6a are monoclinic, a = 11.5210(13), 6 = 10.2860(8), c = 12.7354(15) A, P = olO1 .878(5)", Z = 4, space group P 2 , l c ; and those of 6b are monoclin~c, a = 8.5047 (8)

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Section: Resultsmentioning

confidence: 53%

Structural studies of organoboron compounds. XVIII. Crystal and molecular structures of 2,2-diphenyl-1,3-dioxa-3a-azonia-2-borataindan and 4-cyclohexyl-6-methyl-2,2-diphenyl-1,3-dioxa-3a-azonia-2-borataindan

Kliegel¹,

Nanninga²,

Rettig³

et al. 1983

Can. J. Chem.

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“…25 Ab-initio calculations provide a reasonable correlation for the tautomerization energy estimation. [26][27][28][29] However these calculations are expensive and hard to apply to most of the molecules of real interest, particularly in the biochemical field. Alternatively it is possible to use semiempirical calculations assuming errors of some kcal/mol for the tautomerization energy values.…”

Section: Equationmentioning

confidence: 99%

Tautomerism of lactones and related compounds. Mass spectrometric data and theoretical calculations

Allegretti¹,

Cortizo²,

Guzmán³

et al. 2003

Arkivoc

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The enolization degree of lactones and esters is favoured by the oxygen-sulfur exchange in the respective functional groups. The analysis of the corresponding mass spectra has allowed unambiguous assignment of some fragments to specific tautomers and establishment of an acceptable correlation between ion abundances ratios and AM1 theoretical calculations. This supports mass spectrometry as an adequate tool to evaluate the tautomerism of neutral species.

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“…The tautomeric system 2(1H)-pyridone ++ 2-hydroxypyridine 1 has been the subject of several experimental and theoretical studies (1)(2)(3)(4)(5)(6). The alkylation of this bifunctional nucleophile still appears to be somewhat puzzling in spite of a number of detailed studies.…”

Section: Introductionmentioning

confidence: 99%

Structural studies of organoboron compounds XXIII: preparation and crystal and molecular structures of 2,2-diphenyl-1,3-dioxa-4a- azonia-2-borata-1,2,3,4-tetrahydronaphthalene and 4,4-diphenyl-3-oxa-1-aza-4a-azonia-4-borata-1,2,3,4-tetrahydronaphthalene

Kliegel¹,

Motzkus²,

Nanninga³

et al. 1986

Can. J. Chem.

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. Can. J. Chem. 64, 507 (1986). Details of the synthesis, physical properties, and the crystal molecular structures of 2,2-diphenyl-l,3-dioxa-4a-azonia-2-borata-1,2,3,4-tetrahydronaphthalene, 5, and 4,4-diphenyl-3-oxa-l-aza-4a-azonia-4-borata-l,2,3,4-tetrahydronaphthalene, 9, are reported. Crystals of 5 are monoclinic, a = 9.972(1), b = 11.848(1), c = 13.561(2) A, P = 106.231(5)", Z = 4, space group P21/c and those of 9 are orthorhombic, a = 20.676(1), b = 15.4199(9), c = 9.7533(4) A, Z = 8, space group Pbca. Both structures were solved by direct methods and were refined by full-matrix least-squares procedures to R values of 0.036 and 0.045 for 1060 and 1700 reflections with I 2 3u(4 respectively. Compound 5 has the expected cyclic B,N-betaine structure, resulting from N-aklylation of 2(1H)-pyridone with formaldehyde followed by reaction with (Ph2B)20. The aza analog, however, does not have the analogous structure. The alkylation of 2-aminopyridine with formaldehyde in the presence of (Ph2B)20 yields 9, derived from alkylation of the amine rather than the pyridine ring nitrogen atom. [Traduit par le journal]

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Tautomerization of formamide, 2-pyridone, and 4-pyridone: an ab initio study

Cited by 200 publications

References 1 publication

Structural studies of organoboron compounds. XVIII. Crystal and molecular structures of 2,2-diphenyl-1,3-dioxa-3a-azonia-2-borataindan and 4-cyclohexyl-6-methyl-2,2-diphenyl-1,3-dioxa-3a-azonia-2-borataindan

Structural studies of organoboron compounds. XVIII. Crystal and molecular structures of 2,2-diphenyl-1,3-dioxa-3a-azonia-2-borataindan and 4-cyclohexyl-6-methyl-2,2-diphenyl-1,3-dioxa-3a-azonia-2-borataindan

Tautomerism of lactones and related compounds. Mass spectrometric data and theoretical calculations

Structural studies of organoboron compounds XXIII: preparation and crystal and molecular structures of 2,2-diphenyl-1,3-dioxa-4a- azonia-2-borata-1,2,3,4-tetrahydronaphthalene and 4,4-diphenyl-3-oxa-1-aza-4a-azonia-4-borata-1,2,3,4-tetrahydronaphthalene

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