Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Matrix Infrared Spectra and DFT Computations of CH2CNH and CH2NCH Produced from CH3CN by Laser-Ablation Plume Radiation

  • Received : 2012.11.22
  • Accepted : 2013.02.05
  • Published : 2013.05.20
Download PDF
⟨ Previous Next ⟩

Abstract

The smallest ketenimine and hydrogen cyanide N-methylide ($CH_2CNH$ and $CH_2NCH$) are provided from the argon/acetonitrile matrix samples exposed to radiation from laser ablation of transition-metals. New infrared bands are observed in addition to better determination of the vibrational characteristics for the previously reported bands, and the $^{13}C$ substituted isotopomers ($^{13}{CH_2}^{13}CNH$ and $^{13}CH_2N^{13}CH$) are also generated. Density functional frequency calculations and the D and $^{13}C$ isotopic shifts substantiate the vibrational assignments. $CH_2CNH$ is probably produced through single-step conversion of $CH_3CN$, whereas $CH_2NCH$ through two-step conversion via 2H-azirine. Inter-conversions between these two products evidently do not occur during photolysis and annealing.

Keywords

References

  1. Sandholm, S. T.; Bjarnov, E.; Schwendeman, R. H. J. Mol. Spectrosc. 1982, 95, 276-287. https://doi.org/10.1016/0022-2852(82)90128-X
  2. Kukolich, S. G. J. Chem. Phys. 1982, 76, 997-1006. https://doi.org/10.1063/1.443070
  3. Sassi, P.; Paliani, G.; Cataliotti, R. S. J. Chem. Phys. 1998, 108, 10197-10205. https://doi.org/10.1063/1.476479
  4. Deng, R.; Trenary, M. J. Phys. Chem. C 2007, 111, 17088-17093. (MeCN isomers). https://doi.org/10.1021/jp075668f
  5. Yang, X.; Maeda, S.; Ohno, K. J. Phys. Chem. A 2005, 109, 7319-7358. https://doi.org/10.1021/jp052067k
  6. Fan, L.; Ziegler, T. J. Chem. Phys. 1990, 92, 3645-3652. (PES of $CH_{3}NC$). https://doi.org/10.1063/1.457820
  7. Hattori, R.; Suzuki, E.; Shimizu, K. J. Mol. Struct. 2005, 738, 165-170. ($CH_{3}NC$). https://doi.org/10.1016/j.molstruc.2004.11.068
  8. Moran, S.; Ellis, H. B., Jr.; DeFrees, D. J.; McLean, A. D.; Ellison, G. B. J. Am. Chem. Soc. 1987, 109, 5996-6003. https://doi.org/10.1021/ja00254a018
  9. Svejda, P.; Volman, D. H. J. Phys. Chem. 1970, 74, 1872-1875. https://doi.org/10.1021/j100704a008
  10. Egland, R. J.; Symons, M. R. C. J. Chem. Soc. A 1970, 5, 1326-1329. ($H_{2}CNC$).
  11. Moran, S.; Ellis, H. B., Jr.; DeFrees, D. J.; McLean, A. D.; Paulson, S. E.; Ellison, G. B. J. Am. Chem. Soc. 1987, 109, 6004- 6010. https://doi.org/10.1021/ja00254a019
  12. Hirao, T.; Ozeki, H.; Saito, S.; Yamamoto, S. J. Chem. Phys. 2007, 127, 134312-1-7. ($H_{2}CNC$). https://doi.org/10.1063/1.2776267
  13. Maier, G.; Reisenauser, H. P.; Rademacher, K. Chem. Eur. J. 1998, 4, 1957-1963. https://doi.org/10.1002/(SICI)1521-3765(19981002)4:10<1957::AID-CHEM1957>3.0.CO;2-1
  14. Dendramis, A.; Leroi, G. E. J. Chem. Phys. 1977, 66, 4334-4341. https://doi.org/10.1063/1.433724
  15. Nimlos, M. R.; Davico, G.; Geise, C. M.; Wenthold, P. G.; Blanksby, W. C.; Lineberger, S. J.; Hadad, C. M.; Petersson, G. A.; Ellison, G. B. J. Chem. Phys. 2002, 117, 4323-4340. https://doi.org/10.1063/1.1496473
  16. Jacox, M. E. J. Phys. Chem. Ref. Data 2003, 32, 1-441. (HCCN, HCNC, & cyc-HCNC). https://doi.org/10.1063/1.1497629
  17. Jacox, M. E. Chem. Phys. 1979, 43, 157-172. https://doi.org/10.1016/0301-0104(79)85184-8
  18. Jacox, M. E.; Milligan, D. E. J. Am. Chem. Soc. 1963, 85, 278-282. https://doi.org/10.1021/ja00886a006
  19. Maier, G.; Schmidt, C.; Reisenauer, H. P.; Endlein, E.; Becker, D; Eckwert, J.; Hess, B. A.; Schaad, L. J. Chem. Ber. 1993, 126, 2337-2352. https://doi.org/10.1002/cber.19931261024
  20. Cho, H.-G.; Andrews, L. J. Phys. Chem. 2011, 115, 8638-8642. https://doi.org/10.1021/jp204887y
  21. Andrews, L.; Kushto, G. P.; Zhou, M.; Willson, S. P.; Souter, P. F. J. Chem. Phys. 1999, 110, 4457-4466. https://doi.org/10.1063/1.478329
  22. Andrews, L.; Cho, H.-G. Organometallics 2006, 25, 4040-4053. (Review article). https://doi.org/10.1021/om060318l
  23. Cho, H.-G.; Andrews, L. J. Am. Chem. Soc. 2008, 130, 15836-15841. https://doi.org/10.1021/ja805862j
  24. Zhou, M.; Chen, M.; Zhang, L.; Lu, H. J. Phys. Chem. A 2002, 106, 9017-9023. https://doi.org/10.1021/jp020971w
  25. Cho, H.-G.; Andrews, L. Dalton Trans. 2011, 40, 11115-11124. https://doi.org/10.1039/c0dt01827a
  26. Andrews, L.; Citra, A. Chem. Rev. 2002, 102, 885-911. https://doi.org/10.1021/cr0000729
  27. Andrews, L. Chem. Soc. Rev. 2004, 33, 123-132. https://doi.org/10.1039/b210547k
  28. Cho, H.-G.; Andrews, L. J. Phys. Chem. A 2010, 114, 891-897. https://doi.org/10.1021/jp9099368
  29. Cho, H.-G.; Andrews, L. J. Phys. Chem. A 2010, 114, 5997-6006. https://doi.org/10.1021/jp1012686
  30. Cho, H.-G.; Andrews, L. J. Organomet. Chem. 2012, 703, 25-33. https://doi.org/10.1016/j.jorganchem.2011.12.007
  31. Cho, H.-G.; Andrews, L. Organometallics 2011, 31, 535-544.
  32. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; et al. Gaussian 09, Revision A.02, Gaussian, Inc.: Wallingford, CT, 2009.
  33. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652. https://doi.org/10.1063/1.464913
  34. Lee, C.; Yang, Y.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789. https://doi.org/10.1103/PhysRevB.37.785
  35. Burke, K.; Perdew, J. P.; Wang, Y. In Electronic Density Functional Theory: Recent Progress and New Directions; Dobson, J. F., Vignale, G., Das, M. P., Eds.; Plenum: 1998.
  36. Fukui, K. Acc. Chem. Res. 1981, 14, 363-368. https://doi.org/10.1021/ar00072a001

Cited by

  1. Computational Study on the Vinyl Azide Decomposition vol.118, pp.27, 2014, https://doi.org/10.1021/jp500140j
  2. DFT Studies on Two Novel Explosives Based on the Guanidine-Fused Bicyclic Structure vol.35, pp.4, 2014, https://doi.org/10.5012/bkcs.2014.35.4.1043
  3. Matrix Infrared Spectra and DFT Computations of 2H-Azirine Produced from Acetonitrile by Laser-Ablation Plume Radiation vol.35, pp.7, 2014, https://doi.org/10.5012/bkcs.2014.35.7.2093
  4. CN in the Gas Phase vol.120, pp.28, 2016, https://doi.org/10.1021/acs.jpca.6b04733
  5. Formation of methyl ketenimine (CH3CH = C = NH) and ethylcyanide (CH3CH2C≡N) isomers through successive hydrogenations of acrylonitrile (CH2 = CH − C≡N) under interstellar conditions: The rol vol.485, pp.4, 2013, https://doi.org/10.1093/mnras/stz698
  6. Determination of [CH3NC]/[H2C═C═NH] Abundance Ratios from N + CH3CN Solid Phase Reaction in the Temperature Range from 10 to 40 K: Application to the Com vol.3, pp.6, 2019, https://doi.org/10.1021/acsearthspacechem.9b00044
  7. SERS-Active Cu Nanoparticles on Carbon Nitride Support Fabricated Using Pulsed Laser Ablation vol.9, pp.9, 2013, https://doi.org/10.3390/nano9091223
  8. Computational Study of the Ene/Rearrangement Reaction between (F3C)2B═NMe2, 1, and Acetonitrile: Reactant-Catalyzed Mechanism of the Ketenimine-Nitrile-Like Rea vol.123, pp.43, 2013, https://doi.org/10.1021/acs.jpca.9b09403