Investigation of the Vibrational Characteristics of 6-Isocyano-1-Methyl-1H-Indole: Utilizing the Isonitrile Group as an Infrared Probe-Reference-Cited by-同舟云学术

Investigation of the Vibrational Characteristics of 6-Isocyano-1-Methyl-1H-Indole: Utilizing the Isonitrile Group as an Infrared Probe

Published:2023-10-05 Issue:19 Volume:28 Page:6939
ISSN:1420-3049
Container-title:Molecules
language:en
Short-container-title:Molecules

Author:

You Min¹,Gao Zilin¹,Zhou Liang²,Guo Changyuan³,Guo Qiang⁴

Affiliation:

1. School of Computer Science and Engineering, Chongqing Three Gorges University, Wanzhou, Chongqing 404100, China

2. Department of Physics and Applied Optics Beijing Area Major Laboratory, Center for Advanced Quantum Studies, Beijing Normal University, Beijing 100875, China

3. Key Laboratory of Intelligent Air-Ground Cooperative Control for Universities in Chongqing, College of Automation, Chongqing University of Posts and Telecommunications, Chongqing 400065, China

4. Shanxi Province Key Laboratory of Higee-Oriented Chemical Engineering, School of Chemistry and Chemical Engineering, North University of China, Taiyuan 030051, China

Abstract

Indole derivatives have garnered considerable attention in the realm of biochemistry due to their multifaceted properties. In this study, we undertake a systematic investigation of the vibrational characteristics of a model indole derivative, 6-isocyano-1-methyl-1H-indole (6ICMI), by employing a combination of FTIR, IR pump-probe spectroscopy, and theoretical calculations. Our findings demonstrate a strong dependence of the isonitrile stretching frequency of 6ICMI on the polarizability of protic solvents and the density of hydrogen-bond donor groups in the solvent when the isonitrile group is bonded to aromatic groups. Both experimental and theoretical analyses unveil a significant correlation between the isonitrile stretch vibration of 6ICMI and the solvent acceptor number of alcohols. Furthermore, the polarization-controlled infrared pump-probe conducted on 6ICMI in dimethyl sulfoxide provides additional support for the potential use of the isonitrile stretching mode of 6ICMI as an effective infrared probe for local environments.

Funder

Scientific and Technological Research Program of Chongqing Municipal Education Commission;Foundation of Intelligent Ecotourism Subject Group of Chongqing Three Gorges University

Publisher

MDPI AG

Subject

Chemistry (miscellaneous),Analytical Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Molecular Medicine,Drug Discovery,Pharmaceutical Science

Link

https://www.mdpi.com/1420-3049/28/19/6939/pdf

Reference37 articles.

1. Gummidi, L., Kerru, N., Awolade, P., Raza, A., Sharma, A.K., and Singh, P. (2020). Synthesis of indole-tethered [1, 3, 4] thiadiazolo and [1, 3, 4] oxadiazolo [3, 2-a] pyrimidin-5-one hybrids as anti-pancreatic cancer agents. Bioorg. Med. Chem. Lett., 30.

2. Siddiqui, S.K., SahayaSheela, V.J., Kolluru, S., Pandian, G.N., Santhoshkumar, T.R., Dan, V.M., and Ramana, C.V. (2020). Discovery of 3-(benzofuran-2-ylmethyl)-1H-indole derivatives as potential autophagy inducers in cervical cancer cells. Bioorg. Med. Chem. Lett., 30.

3. Chemoproteomics of an indole-based quinone epoxide identifies druggable vulnerabilities in vancomycin-resistant Staphylococcus aureus;Kulkarni;J. Med. Chem.,2019

4. One-pot synthesis and molecular docking of some new spiropyranindol-2-one derivatives as immunomodulatory agents and in vitro antimicrobial potential with DNA gyrase inhibitor;Salem;Eur. J. Med. Chem.,2020

5. Scaffold simplification strategy leads to a novel generation of dual human immunodeficiency virus and enterovirus-A71 entry inhibitors;Sun;J. Med. Chem.,2019