Author | dc.contributor.author | Zapata Torres, Gerald Amilcar | |
Author | dc.contributor.author | Cassels Niven, Bruce | es_CL |
Author | dc.contributor.author | Parra Mouchet, Julia | es_CL |
Author | dc.contributor.author | Mascarenhas, Yvonne P. | es_CL |
Author | dc.contributor.author | Ellena, Javier | es_CL |
Author | dc.contributor.author | De Araujo, A. S. | es_CL |
Admission date | dc.date.accessioned | 2010-01-26T20:33:26Z | |
Available date | dc.date.available | 2010-01-26T20:33:26Z | |
Publication date | dc.date.issued | 2008-06 | |
Cita de ítem | dc.identifier.citation | Journal of Molecular Graphics and Modelling, Volume 26, Issue 8, , Pages 1296-1305, 2008 | en_US |
Identifier | dc.identifier.issn | 1093-3263 | |
Identifier | dc.identifier.uri | https://repositorio.uchile.cl/handle/2250/120868 | |
Abstract | dc.description.abstract | Time-averaged conformations of ( )-1-[3,4-(methylenedioxy)phenyl]-2-methylaminopropane hydrochloride (MDMA, ‘‘ecstasy’’) in D2O,
and of its free base and trifluoroacetate in CDCl3, were deduced from their 1H NMR spectra and used to calculate their conformer distribution.
Their rotational potential energy surface (PES) was calculated at the RHF/6-31G(d,p), B3LYP/6-31G(d,p), B3LYP/cc-pVDZ and AM1 levels.
Solvent effects were evaluated using the polarizable continuum model. TheNMR and theoretical studies showed that, in the free base, the N-methyl
group and the ring are preferentially trans. This preference is stronger in the salts and corresponds to the X-ray structure of the hydrochloride.
However, the energy barriers separating these forms are very low. The X-ray diffraction crystal structures of the anhydrous salt and its monohydrate
differed mainly in the trans or cis relationship of the N-methyl group to the a-methyl, although these two forms interconvert freely in solution. | en_US |
Patrocinador | dc.description.sponsorship | This work was supported by Proyecto INI 06/03-2
Universidad de Chile, Proyecto Conicyt Bicentenario de
Insercion Academica-2004, FONDECYT grant 2000009, the
Presidential Chair in Sciences (BKC), and ICM grant no. P99-
031-F (Chile), and FAPESP and CNPq (Brazil). YPM and JE
are grateful to CNPq for research fellowships. | en_US |
Lenguage | dc.language.iso | en | en_US |
Publisher | dc.publisher | Elsevier Inc | en_US |
Keywords | dc.subject | MDMA | en_US |
Título | dc.title | Quantum-chemical, NMR and X-ray diffraction studies on (±)-1-[3,4-(methylenedioxy)phenyl]-2-methylaminopropane | en_US |
Document type | dc.type | Artículo de revista | |