Issue 23, 2013
From the journal:

CrystEngComm

New acentric materials constructed from aminopyridines and 4-nitrophenol†

Sergiu Draguta,a   Marina S. Fonari,ab   Artëm E. Masunov,c   Joel Zazueta,a   Shannon Sullivan,c   Mikhail Yu. Antipin‡ad  and  Tatiana V. Timofeeva*a  

* Corresponding authors

a Department of Chemistry & Biology, New Mexico Highlands University, Las Vegas, NM 87701, USA
E-mail: tvtimofeeva@nmhu.edu

b Institute of Applied Physics Academy of Sciences of Moldova, Academy str. 5, MD2028, Chisinau, Moldova

c NanoScience Technology Center, Department of Chemistry, Department of Physics, and Florida Solar Energy Center, University of Central Florida, Orlando, FL 32826, USA

d A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov str. 28, 119991 Moscow, Russia

Abstract

Co-crystallization of 4-nitrophenol (I) with five aminopyridines (4-aminopyridine 1, 3,4-diaminopyridine 2, 2,3-diaminopyridine 3, 3-aminopyridine 4, 2-amino-6-methylpyridine 5) and 2,4-diaminopyrimidine 6 resulted in six adducts with the ratio of components 2 : 1 in five and 1 : 1 in one final compounds. Single crystals were grown by slow evaporation technique using ethanol as a solvent. Five adducts with 1–5 crystallize in acentric P21 and Pna21 space groups, and one, 2(I)·6 – in centrosymmetric P21/c space group. Compounds 2(I)·1, 2(I)·2, 2(I)·3 are isomorphous, and demonstrate similar H-bonding patterns despite the differences in aminopyridine molecules. Compound 2(I)·5 is isomorphous to two previously reported compounds. Adducts 2(I)·1, 2(I)·2, 2(I)·3, 2(I)·5, 2(I)·6 represent organic salts composed of pyridinium/pyrimidinium cation, 4-nitrophenolate anion, and 4-nitrophenol neutral molecule. The H-bonded 4-nitrophenol–4-nitrophenolate anionic dimers were found in all compounds with 2 : 1 molar ratio. In adduct I·4 both molecules are in neutral form. The IR spectral data support crystallographic conclusions on salts formation. Plane wave pseudopotential density functional theory calculations were used to predict hyperpolarizability tensor components. Our calculations suggest 2(I)·3 as the best candidate for nonlinear optical materials (14 times more active than urea).

Graphical abstract: New acentric materials constructed from aminopyridines and 4-nitrophenol

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C3CE40291F
Article type
Paper
Submitted
15 Feb 2013
Accepted
10 Apr 2013
First published
11 Apr 2013

CrystEngComm, 2013,15, 4700-4710

Permissions

Request permissions

New acentric materials constructed from aminopyridines and 4-nitrophenol

S. Draguta, M. S. Fonari, A. E. Masunov, J. Zazueta, S. Sullivan, M. Yu. Antipin and T. V. Timofeeva, CrystEngComm, 2013, 15, 4700 DOI: 10.1039/C3CE40291F

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements