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Theoretical investigation on the water-assisted excited-state proton transfer of 7-azaindole derivatives: substituent effect

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Abstract

A systematic study on the first excited-state proton transfer (ESPT) in 2RAI-H2O (R = OH, OCH3, CN, NO2, CHO) complexes in solution were investigated at the TD-M06-2X/6-31 + G(d, p) level. The double proton transfer occurred in an asynchronous but concerted protolysis fashion no matter which substituent R was used at C2 position in pyrrole ring in the 7AI-H2O complex. The specific vibrational-mode of ESPT in the model systems was confirmed and contributed to promote the reaction rate by shortening the reaction path. The substituent effects of different groups on the ESPT thermodynamics and kinetics were discussed. It was obvious that the geometries, barrier height, asynchrony, and specific vibration-mode of excited-state proton transfer changed with the different substituent groups.

The distance between two neighboring heavy atoms such as N1-O11 (R1) and O11-N8 (R2) distances played an important role in the proton transfer reaction. The sum of the N1-O11 and O11-N8 distances in the reactant of 2RAI-H2O (R=H, OH, OCH3; CN, CHO, NO2) complexes is in the range of 5.542 Å~5.692 Å and changes along with the substituent group at C2 position in the pyrrole ring. The ESDPT barrier height and the sum of the N1-O11 and O11-N8 distances have a good correlation.

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  • 03 November 2017

    The original version of this article unfortunately contained a mistake in Table 3. This correct Table 3 is given below.

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Acknowledgements

This work was supported by grants from the National Natural Science Foundation of China (21403114), the Natural Science Foundation of Jiangsu province (BK20140970), and the Scientific Research Foundation for the Returned Overseas Chinese Scholars, state Education Ministry.

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  1. Department of Chemistry and Material Science, College of Science, Nanjing Forestry University, Nanjing, 210037, People’s Republic of China

    Jiacheng Yi & Hua Fang

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  1. Jiacheng Yi
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Correspondence to Hua Fang.

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A correction to this article is available online at https://doi.org/10.1007/s00894-017-3506-6.

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Yi, J., Fang, H. Theoretical investigation on the water-assisted excited-state proton transfer of 7-azaindole derivatives: substituent effect. J Mol Model 23, 312 (2017). https://doi.org/10.1007/s00894-017-3487-5

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