...

Evaluation of intermolecular interactions in thioxanthone derivatives

by user

on
Category:

science

21

views

Report

Comments

Transcript

Evaluation of intermolecular interactions in thioxanthone derivatives
Title: Evaluation of intermolecular interactions in thioxanthone derivatives: substituent effect on crystal
diversity
1
1,2
1,3
Author(s): Jacob, C. ; da Piedade, Fátima M. ; Paula Robalo, M. ; Teresa Duarte, M.
1
Source: Crystengcomm
Volume: 13 Issue: 7 Pages: 2604-2616 DOI: 10.1039/c0ce00783h Published: 2011
Document Type: Article
Language: English
Abstract: A family of 9H-thioxanthen-9-one derivatives and two precursors, 2-[(4-bromophenyl)
sulfanyl]-5-nitrobenzoic acid and 2-[(4-aminophenyl) sulfanyl]-5-nitrobenzoic acid, were synthesized and
studied in order to assess the role of the different substituent groups in determining the supramolecular
motifs. From our results we can conclude that Etter's rules are obeyed: whenever present the -COOH
head to head strong hydrogen bonding dimer, R-2(2)(8) synthon, prevails as the dominant interaction.
As for -NH2, the best donor when present also follows the expected hierarchy, an NH center dot center
dot center dot O(COOH) was formed in the acid precursor (2) and an NH center dot center dot center
dot O(C=O) in the thioxanthone (4). The main role played by weaker hydrogen bonds such as CH center
dot center dot center dot O, and other intermolecular interactions, pi-pi and Br center dot center dot
center dot O, as well as the geometric restraints of packing patterns shows the energetic interplay
governing crystal packing. A common feature is the relation between the p-p stacking and the unit cell
dimensions. A new synthon notation, R`, introduced in this paper, refers to the possibility of accounting
for intra- and intermolecular interactions into recognizable and recurring aggregate patterns.
KeyWords Plus: Hydrogen-Bond Patterns; Organic-Compounds; CH/PI Interaction; C-H; Recognition;
Complexes; Molecules; Chemistry; Database; Network
Reprint Address: Duarte, MT (reprint author), Univ Tecn Lisboa, Inst Super Tecn, Ctr Quim Estrutural, Av
Rovisco Pais, P-1049001 Lisbon, Portugal.
Addresses:
1. Univ Tecn Lisboa, Inst Super Tecn, Ctr Quim Estrutural, P-1049001 Lisbon, Portugal
2. FCUL, Dept Quim & Bioquim, P-1749016 Lisbon, Portugal
3. Inst Super Engn Lisboa, Dept Engn Quim, P-1959007 Lisbon, Portugal
E-mail Address: [email protected]
Funding:
Funding Agency
Grant Number
Fundação para a Ciência e a Tecnologia (FCT), Portugal
PPCDT/QUI/58791/2004
PTDC/QUI/65379/2006
FCT
SFRH/BD/14367/2003
Publisher: Royal Soc Chemistry
ISEL – Instituto Superior de Engenharia de Lisboa
SDP - Serviço de Documentação e Publicações
Publisher Address: Thomas Graham House, Science Park, Milton RD, Cambridge CB4 0WF, Cambs,
England
ISSN: 1466-8033
Citation: JACOB, C.; da PIEDADE, Fátima M.; ROBALO, M. Paula; DUARTE, M. Teresa - Evaluation of
intermolecular interactions in thioxanthone derivatives: substituent effect on crystal diversity.
Crystengcomm. ISSN 1466-8033. Vol. 13, n.º7 (2011) 2604-2616.
ISEL – Instituto Superior de Engenharia de Lisboa
SDP - Serviço de Documentação e Publicações
Fly UP