Journal article
Edge-to-Edge C–H···N Hydrogen Bonds in Two-Component Co-crystals Aide a [2 + 2] Photodimerization
Crystal growth & design, Vol.17(4), pp.2054-2058
04/05/2017
DOI: 10.1021/acs.cgd.7b00040
Abstract
C-H···N hydrogen bonds support an intermolecular [2 + 2] photodimerization in the solid state. The photocycloaddition occurs in a co-crystal of composition (tbrb)·(4,4′-bpe) (where tbrb = 1,2,4,5-tetrabromobenzene; 4,4′-bpe = trans-1,2-bis(4-pyridyl)ethylene) that consists of one-dimensional (1D) chains that self-assemble to form corrugated sheets. Stacking of 4,4′-bpe between sheets conforms to the topochemical postulate of Schmidt. The alkene reacts to form rctt-tetrakis(4-pyridyl)cyclobutane (4,4′-tpcb) stereoselectively and in quantitative yield. C-H···N hydrogen bonds also support the assembly of the components in (tbrb)·(4,4′-azo) (where: 4,4′-azo = 4,4′-azopyridine) into planar sheets. Density-functional theory calculations reveal identical face-to-face stacks of tbrb to aide in the stabilization of the structures of the co-crystals.
Details
- Title: Subtitle
- Edge-to-Edge C–H···N Hydrogen Bonds in Two-Component Co-crystals Aide a [2 + 2] Photodimerization
- Creators
- Cristian M Santana - Department of Biological Sciences, Webster University, St. Louis, Missouri 63119, United StatesEric W Reinheimer - Rigaku Americas Corporation, The Woodlands, Texas 77381, United StatesHerman R Krueger - Department of Biological Sciences, Webster University, St. Louis, Missouri 63119, United StatesLeonard R MacGillivray - Department of Chemistry, University of Iowa, Iowa City, Iowa 52242, United StatesRyan H Groeneman - Department of Biological Sciences, Webster University, St. Louis, Missouri 63119, United States
- Resource Type
- Journal article
- Publication Details
- Crystal growth & design, Vol.17(4), pp.2054-2058
- DOI
- 10.1021/acs.cgd.7b00040
- ISSN
- 1528-7483
- eISSN
- 1528-7505
- Grant note
- DOI: 10.13039/100000078, name: Division of Materials Research, award: DMR-1408834; name: Faculty Development Fund, Webster University
- Language
- English
- Date published
- 04/05/2017
- Academic Unit
- Chemistry; Pharmaceutical Sciences and Experimental Therapeutics
- Record Identifier
- 9984216598202771
Metrics
4 Record Views