TY - JOUR
T1 - Infrared spectroscopic investigations of cationic ethanol, propanol, and butanol
AU - Matsuda, Yoshiyuki
AU - Harigaya, Hiroyuki
AU - Xie, Min
AU - Takahashi, Kaito
AU - Fujii, Asuka
N1 - Funding Information:
We thank Dr. T. Maeyama for his helpful discussions. YM acknowledges support from the Sumitomo Foundation and the Grant-in-Aid for Scientific Research (Project No. 26108504 on Innovative Area [2507]) from MEXT Japan. AF acknowledges the Grant-in-Aid for Scientific Research (Project No. 26288002) from JSPS . KT thanks Academia Sinica, National Center for High Performance Computing of Taiwan and National Science Council (NSC 102-2113-M-001-012-MY3) of Taiwan for support.
Publisher Copyright:
© 2015 Elsevier B.V. All rights reserved.
PY - 2015/11/1
Y1 - 2015/11/1
N2 - Infrared spectroscopy of the alcohol cations of ethanol, propanol, and butanol was performed to investigate their structures and hyperconjugation mechanisms. In the ethanol cation, the C-C bond hyperconjugates with the singly occupied molecular orbital (SOMO) at the oxygen atom, so that the C-C bond weakens and the bond length elongates. Multiple hyperconjugations among SOMO, the C-C bond, and the end C-H bond occur in the propanol cation and enhance the acidity of the C-H bond through the delocalization of its bonding σ electron. The butanol cation forms the oxonium-type structure through the proton transfer from the terminal CH bond.
AB - Infrared spectroscopy of the alcohol cations of ethanol, propanol, and butanol was performed to investigate their structures and hyperconjugation mechanisms. In the ethanol cation, the C-C bond hyperconjugates with the singly occupied molecular orbital (SOMO) at the oxygen atom, so that the C-C bond weakens and the bond length elongates. Multiple hyperconjugations among SOMO, the C-C bond, and the end C-H bond occur in the propanol cation and enhance the acidity of the C-H bond through the delocalization of its bonding σ electron. The butanol cation forms the oxonium-type structure through the proton transfer from the terminal CH bond.
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U2 - 10.1016/j.cplett.2015.10.044
DO - 10.1016/j.cplett.2015.10.044
M3 - Article
AN - SCOPUS:84946822987
SN - 0009-2614
VL - 640
SP - 215
EP - 218
JO - Chemical Physics Letters
JF - Chemical Physics Letters
ER -