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Experimental Evidence for Intramolecular Blue-Shifting C−H···O Hydrogen Bonding by Matrix-Isolation Infrared Spectroscopy
Abstract
Experimental evidence for intramolecular blue-shifting C-H...O hydrogen bonding is presented. Argon matrix-isolation infrared spectra of 1-methoxy-2-(dimethylamino)ethane exhibit a band at 3016.5 cm-1. Spectral behavior with annealing indicates that this band is assigned to the most stable conformer, trans-gauche-(trans|gauche'), with an intramolecular C-H...O hydrogen bond. Density functional calculations show that this band arises from the stretching vibration of the C-H bond participating in the formation of the C-H...O hydrogen bond. The C-H bond is shortened by 0.004 A, and the C-H stretching band is blue-shifted by at least 35 cm-1 on the formation of the hydrogen bond. The (C)H...O distance is calculated as 2.38 A, which is shorter than the corresponding van der Waals separation by 0.3 A.
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Cited by
Takahashi, O., Kohno, Y., & Nishio, M. (2010) · Chemical Reviews · doi:10.1021/cr100072x · Cited by 583
Zhang, J., Sato, H., Tsuji, H., Noda, I., & Ozaki, Y. (2005) · Macromolecules · doi:10.1021/ma047872w · Cited by 395
Spectroscopic analysis and DFT calculations of a food additive Carmoisine
Snehalatha, M., Ravikumar, C., Hubert Joe, I., Sekar, N., & Jayakumar, V. S. (2009) · Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy · doi:10.1016/j.saa.2008.11.017 · Cited by 337
Sato, H., Miyada, M., Yamamoto, S., Raghunatha Reddy, K., & Ozaki, Y. (2016) · RSC Advances · doi:10.1039/c5ra19900j · Cited by 56
Metadata
- Authors
- Matsuura, H., Yoshida, H., Hieda, M., Yamanaka, S.-Y., Harada, T., Shin-ya, K., & Ohno, K.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2003-10-24
- Volume
- 125
- Issue
- 46
- Pages
- 13910-13911
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2028446761
- Cited by
- 194
- References
- 0
- FWCI
- 11.60
- Type
- journal article
- Language
- en
- Open access
- closed
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- Matsuura, H., Yoshida, H., Hieda, M., Yamanaka, S.-Y., Harada, T., Shin-ya, K., & Ohno, K. (2003). Experimental Evidence for Intramolecular Blue-Shifting C−H···O Hydrogen Bonding by Matrix-Isolation Infrared Spectroscopy. Journal of the American Chemical Society. https://doi.org/10.1021/ja030538f
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