Structural analysis of MDMA in solution by methods of chiroptical spectroscopy supported by DFT calculations

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F21%3A43921960" target="_blank" >RIV/60461373:22310/21:43921960 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/60461373:22330/21:43921960 RIV/60461373:22340/21:43921960 RIV/60461373:22810/21:43921960 RIV/00023752:_____/21:43920592

Výsledek na webu

<a href="https://www.sciencedirect.com/science/article/pii/S0924203121000503?via%3Dihub" target="_blank" >https://www.sciencedirect.com/science/article/pii/S0924203121000503?via%3Dihub</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.vibspec.2021.103255" target="_blank" >10.1016/j.vibspec.2021.103255</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Structural analysis of MDMA in solution by methods of chiroptical spectroscopy supported by DFT calculations

Popis výsledku v původním jazyce

Abstract The synthetic drug 3,4-methylenedioxy-N-methylamphetamine (MDMA), also known as ecstasy, is one of the most abused dance drugs spread around the world. The number of seizures of ecstasy tablets increases every year. As MDMA is a chiral substance with one chiral center, it may occur as two enantiomers. These enantiomers have different physiological effects, therefore the reliable detection of individual enantiomers and a detailed structural description are highly desirable. In this work, the 3D structure of MDMA in solution was investigated by vibrational circular dichroism and electronic circular dichroism supplemented by conventional infrared and ultraviolet absorption spectroscopies. The obtained results were supported by density functional theory (DFT) calculations using different levels of theory. Initially, sixty-four starting geometries were optimized at the B3LYP/6-31G(d) level including the solvent effects. Four stable conformers were further reoptimized at higher levels of theory and the spectra were also simulated. The experimental and the calculated spectra were compared via the similarity index. The spectra comparison showed very good agreement, which enabled us to describe the molecular structure of MDMA in detail.

Název v anglickém jazyce

Structural analysis of MDMA in solution by methods of chiroptical spectroscopy supported by DFT calculations

Popis výsledku anglicky

Abstract The synthetic drug 3,4-methylenedioxy-N-methylamphetamine (MDMA), also known as ecstasy, is one of the most abused dance drugs spread around the world. The number of seizures of ecstasy tablets increases every year. As MDMA is a chiral substance with one chiral center, it may occur as two enantiomers. These enantiomers have different physiological effects, therefore the reliable detection of individual enantiomers and a detailed structural description are highly desirable. In this work, the 3D structure of MDMA in solution was investigated by vibrational circular dichroism and electronic circular dichroism supplemented by conventional infrared and ultraviolet absorption spectroscopies. The obtained results were supported by density functional theory (DFT) calculations using different levels of theory. Initially, sixty-four starting geometries were optimized at the B3LYP/6-31G(d) level including the solvent effects. Four stable conformers were further reoptimized at higher levels of theory and the spectra were also simulated. The experimental and the calculated spectra were compared via the similarity index. The spectra comparison showed very good agreement, which enabled us to describe the molecular structure of MDMA in detail.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10406 - Analytical chemistry

Projekt

Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2021

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Vibrational Spectroscopy

ISSN

0924-2031

e-ISSN

—

Svazek periodika

114

Číslo periodika v rámci svazku

MAY 2021

Stát vydavatele periodika

NL - Nizozemsko

Počet stran výsledku

8

Strana od-do

103255

Kód UT WoS článku

000663410900011

EID výsledku v databázi Scopus

2-s2.0-85104589554