Observation of attractive intermolecular C–H⋯O interaction in the crystal packing of 3-chloro- and 3-bromo-2,6-dimethyl-4-nitropyridine N-oxide

Hanuza, J.; Mączka, M.; Waśkowska, A.; Oganowski, W.; Ban-Oganowska, H.; Lutz, Bert; Maas, J.H. van der

doi:10.1016/s0924-2031(96)00071-9

Cited by 22 publications

(5 citation statements)

References 25 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…1303 cm 1 ) 5 and is much larger than that observed for ClDMNPNO and BrDMNPNO (only 10 cm 1 ). 1 Such a result indicates that the C-HÐ Ð ÐO hydrogen bond is stronger for the present compound than BrDMNPNO and ClDMNPNO. This conclusion is consistent with the x-ray study showing that although the HÐ Ð ÐO distances are similar for the three compounds, the C-HÐ Ð ÐO angle is close to 180°in case of BNPNO (176°, see Table 3) whereas the respective angles for ClDMNPNO and BrDMNPNO are 149.4 and 144.9°, respectively.…”

Section: -H· · ·O Bondingmentioning

confidence: 73%

“…The pyridine ring is less deformed than in the other N-oxide derivatives with two methyl groups substituted. 1,15 The mean values of C-C distances and C-C-C angles are now 1.374 (6) …”

Section: Crystal Structurementioning

confidence: 99%

“…This behavior is different from that observed for 4-chloro-2,6-dimethyl-3-iodopyridine N-oxide and 3-chloro-, 3-bromo-and 3-iodo-2,6-dimethyl-4-nitropyridine N-oxides (ClDMNPNO, BrDMNPNO and IDMNPNO, respectively), where almost no bands were observed in this wavenumber region. 1,2,17 It is also worth noting that no bands are …”

Section: Number Of Modes and Assignmentsmentioning

confidence: 99%

“…This conclusion is consistent with the x-ray study showing that although the HÐ Ð ÐO distances are similar for the three compounds, the C-HÐ Ð ÐO angle is close to 180°in case of BNPNO (176°, see Table 3) whereas the respective angles for ClDMNPNO and BrDMNPNO are 149.4 and 144.9°, respectively. 1 Since the C-HÐ Ð ÐO bond strength depends significantly on the bond angle and is the strongest for a linear arrangement of the atoms, 18 the near linear arrangement of the atoms in the case of BNPNO indicates a much stronger bond than for ClDMNPNO and BrDMNPNO.…”

Section: -H· · ·O Bondingmentioning

confidence: 99%

See 3 more Smart Citations

Crystal structure and polarized vibrational spectra of 2‐bromo‐4‐nitropyridine N‐oxide single crystal

Hanuza

Michalski

Mączka

et al. 2002

J Raman Spectroscopy

View full text Add to dashboard Cite

2-Bromo-4-nitropyridine N-oxide is orthorhombic, space group Pbca, with eight molecules per unit cell of dimensions a = 5.979.1/, b = 9.899.1/, c = 23.249.5/Å. The Br ion is nearly coplanar with the pyridine ring, while the two oxygen atoms of the nitro group are displaced above and below the ring by (−0.214Å) and (+0.053Å). The hydrogen bond of the type C -H· · ·O links the molecules into pairs around centers of symmetry. These dimers, arranged into layers related by glide planes, are held together solely by contacts of the van der Waals type. The polarized Fourier transform IR and Raman spectra, measured in the regions 30-3500 and 80-3500 cm −1 , respectively, are correlated with x-ray structural data. Comparison of the spectrum of the dissolved sample with the spectra obtained from the polycrystalline sample and single crystals shows the attractive character of the intermolecular C -H· · ·O contacts for these molecules. The temperature-dependent IR spectra suggest the presence of orientational disorder at higher temperatures.

show abstract

Section: -H· · ·O Bondingmentioning

confidence: 73%

“…The pyridine ring is less deformed than in the other N-oxide derivatives with two methyl groups substituted. 1,15 The mean values of C-C distances and C-C-C angles are now 1.374 (6) …”

Section: Crystal Structurementioning

confidence: 99%

Section: Number Of Modes and Assignmentsmentioning

confidence: 99%

Section: -H· · ·O Bondingmentioning

confidence: 99%

See 2 more Smart Citations

Crystal structure and polarized vibrational spectra of 2‐bromo‐4‐nitropyridine N‐oxide single crystal

Hanuza

Michalski

Mączka

et al. 2002

J Raman Spectroscopy

View full text Add to dashboard Cite

show abstract

“…In particular, the ν s (NO 2 ) band in nitropyridine compounds is intensified by electron-donating substituents of the ring. [1,52] Polarised Raman spectra of the PNMP crystal…”

Section: Nitro Group Vibrationsmentioning

confidence: 99%

Rotational disorder in 2‐piperidyl‐5‐nitro‐6 ‐methylpyridine: structural phase transition and its vibrational characteristics

Lorenc

Palasek

Hanuza

et al. 2008

J Raman Spectroscopy

View full text Add to dashboard Cite

X-ray diffraction (XRD) studies have shown that 2-piperidyl-5-nitro-6-methylpyridine, C 11 H 15 N 3 O 2 , undergoes a structural phase transition at T = 240 K. The room temperature structure is tetragonal, space group I4 1 /a, with the unit-cell dimensions a = 13.993(2) and c = 23.585(5) Å. The pyridine ring takes trans conformation with respect to the piperidine unit. While pyridine is well ordered, the piperidine moiety shows apparent disorder resulting from a libration about the linking N-C bond. The low-temperature phase is monoclinic, space group I2/a. Contraction of the unit-cell volume by 2.3% at 170 K enables the C-H· · ·O linkage between the molecules of the neighbouring stacks. As result, the asymmetric unit becomes bi-molecular. The thermal librations of the piperidine and methyl groups become considerably reduced at 170 K and nearly fully reduced at about 100 K. The IR spectra and polarised Raman spectra agree with the X-ray structure and confirm the disorder effect on the piperidine ring. The assignment of the bands observed was made on the basis of DFT chemical quantum calculations. Copyright

show abstract

Crystal structure of 2,4,6-trinitropyridine and its N-oxide

Zhao

Dong³

2005

J Chem Crystallogr

View full text Add to dashboard Cite

Observation of attractive intermolecular C–H⋯O interaction in the crystal packing of 3-chloro- and 3-bromo-2,6-dimethyl-4-nitropyridine N-oxide

Cited by 22 publications

References 25 publications

Crystal structure and polarized vibrational spectra of 2‐bromo‐4‐nitropyridine N‐oxide single crystal

Crystal structure and polarized vibrational spectra of 2‐bromo‐4‐nitropyridine N‐oxide single crystal

Rotational disorder in 2‐piperidyl‐5‐nitro‐6 ‐methylpyridine: structural phase transition and its vibrational characteristics

Crystal structure of 2,4,6-trinitropyridine and its N-oxide

Contact Info

Product

Resources

About