(2E)-3-(6-Meth­­oxy­naphthalen-2-yl)-1-(pyridin-3-yl)prop-2-en-1-one and its cyclo­condensation product with guanidine, (4RS)-2-amino-4-(6-meth­oxy­naphthalen-2-yl)-6-(pyri­din-3-yl)-3,4-di­hydro­pyrimidine monohydrate: two types of hydrogen-bonded sheet

Nayak, Prakash S. and Narayana, B. and Yathirajan, H. S. and Hosten, Eric C. and Betz, Richard and Glidewell, Christopher (2014) (2E)-3-(6-Meth­­oxy­naphthalen-2-yl)-1-(pyridin-3-yl)prop-2-en-1-one and its cyclo­condensation product with guanidine, (4RS)-2-amino-4-(6-meth­oxy­naphthalen-2-yl)-6-(pyri­din-3-yl)-3,4-di­hydro­pyrimidine monohydrate: two types of hydrogen-bonded sheet. Acta Crystallographica Section C, 70 (11). pp. 1011-1016. ISSN 2053-2296

[img] Text (Full Text)
(2E)-3-(6-Meth­­oxy­naphthalen-2-yl)-1-(pyridin-3-yl).pdf - Published Version
Download (807kB)
Official URL: https://doi.org/10.1107/S2053229614021524

Abstract

The structures of a chalcone and of its cyclo­condensation product with guanidine are reported. In (2E)-3-(6-meth­oxy­naphthalen-2-yl)-1-(pyridin-3-yl)prop-2-en-1-one, C19H15NO2, (I), the planes of the pyridine and naphthalene units make dihedral angles with that of the central spacer unit of 23.61 (13) and 23.57 (15)°, respectively, and a dihedral angle of 47.24 (9)° with each other. The mol­ecules of (I) are linked into sheets by a combination of C—H⋯O and C—H⋯π(arene) hydrogen bonds. In the cyclo­condensation product (4RS)-2-amino-4-(6-meth­oxy­naphthalen-2-yl)-6-(pyri­din-3-yl)-3,4-dihydro­pyrimidine monohydrate, C20H18N4O·H2O, (II), the di­hydro­pyrimidine ring adopts a conformation best described as a shallow boat. The mol­ecular components are linked by two N—H⋯O hydrogen bonds, two O—H⋯N hydrogen bonds and one N—H⋯N hydrogen bond to form complex sheets, with the meth­oxy­naphthalene inter­digitated between inversion-related pairs of sheets.

Item Type: Article
Uncontrolled Keywords: crystal structure, hydrogen bonding, chalcones, cyclocondensation, prop-2-en-1-one, 3,4-dihydropyrimidine, Claisen condensation
Subjects: C Chemical Science > Chemistry
Divisions: Department of > Chemistry
Depositing User: C Swapna Library Assistant
Date Deposited: 02 Nov 2019 10:00
Last Modified: 02 Nov 2019 10:00
URI: http://eprints.uni-mysore.ac.in/id/eprint/9778

Actions (login required)

View Item View Item
uomeprints is powered by EPrints 3 which is developed by the School of Electronics and Computer Science at the University of Southampton. More information and software credits.