An i.r.-spectroscopic study of a postulated C–H ⋯ N hydrogen bond suggested by the X-ray structure of a novel heterocycle

Gorrie, Thomas M.; Haley, Neil F.

doi:10.1039/c39720001081

Cited by 8 publications

(4 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The fact that the crystal structure of one member of the family 5 (R, = R, = H; R, = C,H,, R, = I?-C,H,Br) had been determined (3) increased our interest for the authors suggested an unusual hydrogen bond betwccn amide nitrogen and ortho hydrogen of R,; a sugpestioll that was later challe~lged on the basis of a study of the infrared spectrum (4). It seemed possible that investigation of our compounds, sliould they turn out to be 5, would help to resolve the controversy, for our route has the potential for synthesis of compounds more hindered than, and electronically different from, the few that are known (5).…”

Section: Introductionmentioning

confidence: 99%

Crystal Structure of 1-(Bis-p-chlorophenyl)methylene-3-oxo-4,4-dimethyl-1,2-diazetidmium Hydroxide, Inner Salt, C₁₇H₁₄Cl₂N₂O

Calvo¹,

Ip²,

Krishnamachari³

et al. 1974

Can. J. Chem.

View full text Add to dashboard Cite

1(bis-p-Chlorophenyl)methylene-3-oxo-4,4-dimethyl-1,2-diazetidinium hydroxide, inner salt, C17H14Cl2N2O, crystallizes with orthorhombic symmetry, a = 9.95(1) Å, b = 28.73(2) Å, c = 11.30(1) Å, space group Pbca, Z = 8. The structure of this compound and its isostructural bromine analog were determined. The structure of the chloro-derivative was refined by full-matrix least-squares techniques using 1256 unique reflections to a final R of 0.099. The structure has a short intramolecular C—H … N bond (C … N distance = 2.891(11) Å). One of the phenyl rings is in the same plane as the 4-membered ring whereas the other ring lies in a plane almost perpendicular to this plane. The N—N distance in the heterocyclic ring is 1.415(10) Å, and the N—C distances in the ring are 1.535(11) and 1.377(11) Å. The molecular configuration is stabilized by both the short N … H interaction and delocalization between one of the phenyl groups and the diazetidinium ring.

show abstract

Section: Introductionmentioning

confidence: 99%

Crystal Structure of 1-(Bis-p-chlorophenyl)methylene-3-oxo-4,4-dimethyl-1,2-diazetidmium Hydroxide, Inner Salt, C₁₇H₁₄Cl₂N₂O

Calvo¹,

Ip²,

Krishnamachari³

et al. 1974

Can. J. Chem.

View full text Add to dashboard Cite

show abstract

“…The downfield shifts cited by Fritchie and Wells are more likely to arise from the magnetic anisotropy of the C=N group than from other causes. 23 The infrared spectrum of III is highly complex in the C-H stretching region and we question whether the conclusions drawn by Gorrie and Haley are valid.…”

Section: Description Of the Structurementioning

confidence: 94%

“…-17 (13) -19 (10) C( 2) 1509 ( 22) 983 ( 15) 2647 ( 9) 177 ( 41) 78 ( 18) 14 ( 6) 50 (23) -8( 13) 2( 9)…”

Section: Description Of the Structureunclassified

Evidence for an intramolecular C --H...N hydrogen bond in (E) -5-methylpyridine-2-carboxaldehyde-2'-pyridylhydrazonetetracarbonylmolybdenum(O) from its crystal structure and proton magnetic resonance spectrum

Bruce¹,

Cooper²,

Freeman³

et al. 1974

Inorg. Chem.

View full text Add to dashboard Cite

Bruce, Cooper, Freeman, and McGrath lower barrier than the one we are observing in the proton nmr) involves motion of the hydride ligand through the plane of the phosphorus nuclei rendering the carbonyls equivalent but still maintaining the distinction between the two types of phosphorus. Efforts to observe this process using 13C nmr have been unsuccessful.In summary, although the distinction is not unambiguous, the results tend to favor permutational set II with an exchange intermediate of sufficient concentration to account for the difference between the 90and 220-MHz spectra. Since it appears that dissociation of one end of a chelate ligand is required for a mechanism consistent with set II, it is possible that the intermediate observed is an "arm off' species.Acknowledgment. We would like to thank Mr. G. Watunya and Mr. L. J. Rizzardi for obtaining some of the nmr spectra.Registry No. TaH(CO)2[(CH3)2PCH2CH2P(CH3)2]2, 50600-13-0. Supplementary Material Available. A listing of structure factor amplitudes will appear following these pages in the microfilm edition of this volume of the journal. Photocopies of the supplementary material from this paper only or microfiche (105 X 148 mm, 24X reduction, negatives) containing all of the supplementary material for the papers in this issue may be obtained from the Journals Department,

show abstract

“…c6h5 N-c=o The short distance observed suggested crystal packing forces (54). Studies of aminimides containing the ptoluenesulfonimide group found strong bonds at 1090, 1130, and 1360 cm"1 (10).…”

Section: Physical Propertiesmentioning

confidence: 97%

Chemistry of Aminimides

Wawzonek¹

1980

Ind. Eng. Chem. Prod. Res. Dev.

View full text Add to dashboard Cite

The period 1972-1979 saw considerable activity in research of the chemistry and utilization of aminimides. Studies have extended investigation to aminimides in which the acyl group is derived from imino acids, cyanuric acid, phosphonic acids, and picric acid and to vinylogues of aminimides. Work continued with aminimides derived from nitrogen heterocycles and their conversion to diazepines and bridged nitrogen bicyclic compounds. Commercial utilization of aminimides based on 1,1dimethylhydrazine has been hampered in this country by the loss of the sole commercial source of this compound.

show abstract

An i.r.-spectroscopic study of a postulated C–H ⋯ N hydrogen bond suggested by the X-ray structure of a novel heterocycle

Abstract: 1.r.-spectroscopic methods indicate that the short C-H * -* N distance found in the X-ray structure of 2-1 -(~-bromophenylphenylmethylene)-3-oxo-1,2-diazetidinium inner salt (I) is probably not due to strong hydrogen bonding.

Cited by 8 publications

References 0 publications

Crystal Structure of 1-(Bis-p-chlorophenyl)methylene-3-oxo-4,4-dimethyl-1,2-diazetidmium Hydroxide, Inner Salt, C₁₇H₁₄Cl₂N₂O

Crystal Structure of 1-(Bis-p-chlorophenyl)methylene-3-oxo-4,4-dimethyl-1,2-diazetidmium Hydroxide, Inner Salt, C₁₇H₁₄Cl₂N₂O

Evidence for an intramolecular C --H...N hydrogen bond in (E) -5-methylpyridine-2-carboxaldehyde-2'-pyridylhydrazonetetracarbonylmolybdenum(O) from its crystal structure and proton magnetic resonance spectrum

Chemistry of Aminimides

Contact Info

Product

Resources

About

An i.r.-spectroscopic study of a postulated C–H ⋯ N hydrogen bond suggested by the X-ray structure of a novel heterocycle

Abstract: 1.r.-spectroscopic methods indicate that the short C-H * -* N distance found in the X-ray structure of 2-1 -(~-bromophenylphenylmethylene)-3-oxo-1,2-diazetidinium inner salt (I) is probably not due to strong hydrogen bonding.

Cited by 8 publications

References 0 publications

Crystal Structure of 1-(Bis-p-chlorophenyl)methylene-3-oxo-4,4-dimethyl-1,2-diazetidmium Hydroxide, Inner Salt, C17H14Cl2N2O

Crystal Structure of 1-(Bis-p-chlorophenyl)methylene-3-oxo-4,4-dimethyl-1,2-diazetidmium Hydroxide, Inner Salt, C17H14Cl2N2O

Evidence for an intramolecular C --H...N hydrogen bond in (E) -5-methylpyridine-2-carboxaldehyde-2'-pyridylhydrazonetetracarbonylmolybdenum(O) from its crystal structure and proton magnetic resonance spectrum

Chemistry of Aminimides

Contact Info

Product

Resources

About

Crystal Structure of 1-(Bis-p-chlorophenyl)methylene-3-oxo-4,4-dimethyl-1,2-diazetidmium Hydroxide, Inner Salt, C₁₇H₁₄Cl₂N₂O

Crystal Structure of 1-(Bis-p-chlorophenyl)methylene-3-oxo-4,4-dimethyl-1,2-diazetidmium Hydroxide, Inner Salt, C₁₇H₁₄Cl₂N₂O