Alkyl Spacer Length and Protonation Induced Changes in Crystalline Psychoactive Arylpiperazine Derivatives: Single-Crystal X-ray, Solid-State NMR, and Computational Studies

Edyta Pindelska , Izabela D. Madura , Łukasz Szeleszczuk , Anna Żeszko , Jolanta Jaśkowska , Paulina H. Marek , Wacław Kołodziejski

Abstract

A series of new long-chain arylpiperazine derivatives with a flexible alkyl spacer were synthesized. A controversy concerning the role of the spacer, whether it participates actively in binding to 5-HT1A and D2 receptors or it acts as a distance arm, encouraged us to investigate how the molecular and crystal structure changes with the increased length of the alkyl linker (from four CH2 units to six). In this study both the basic active compounds as well as their hydrochlorides were studied. Single crystal X-ray structure analysis with a combination of 13C, 15N solid state NMR spectroscopy supported by gauge-including projector-augmented wave calculations of chemical shielding was used. These studies were aimed to examine, elucidate, and compare molecular conformations and to point out the most important intermolecular interactions leading to large supramolecular synthons formed in crystals of both bases and hydrochlorides.
Author Edyta Pindelska - [Medical University of Warsaw]
Edyta Pindelska,,
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, Izabela D. Madura (FC / CICSST)
Izabela D. Madura,,
- Chair Of Inorganic Chemistry And Solid State Technology
, Łukasz Szeleszczuk - [Medical University of Warsaw]
Łukasz Szeleszczuk,,
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, Anna Żeszko - [Medical University of Warsaw]
Anna Żeszko,,
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, Jolanta Jaśkowska - [Politechnika Krakowska]
Jolanta Jaśkowska,,
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, Paulina H. Marek (FC / CICSST)
Paulina H. Marek,,
- Chair Of Inorganic Chemistry And Solid State Technology
, Wacław Kołodziejski - [Medical University of Warsaw]
Wacław Kołodziejski,,
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Journal seriesCrystal Growth and Design, ISSN 1528-7483
Issue year2016
Vol16
No11
Pages6371-6380
Publication size in sheets0.5
ASJC Classification3104 Condensed Matter Physics; 2500 General Materials Science; 1600 General Chemistry
DOIDOI:10.1021/acs.cgd.6b00993
URL http://pubs.acs.org/doi/abs/10.1021/acs.cgd.6b00993
Languageen angielski
File
wdpb_publikacje_pliki_plik_publikacja_2958_org.pdf 4.09 MB
Score (nominal)40
Score sourcejournalList
ScoreMinisterial score = 35.0, 31-01-2020, ArticleFromJournal
Ministerial score (2013-2016) = 40.0, 31-01-2020, ArticleFromJournal
Publication indicators Scopus Citations = 5; WoS Citations = 3; Scopus SNIP (Source Normalised Impact per Paper): 2016 = 1.225; WoS Impact Factor: 2016 = 4.055 (2) - 2016=4.054 (5)
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