A Raman Spectroscopic and Computational Study of New Aromatic Pyrimidine-Based Halogen Bond Acceptors

Two new aromatic pyrimidine-based derivatives designed specifically for halogen bond directed self-assembly are investigated through a combination of high-resolution Raman spectroscopy, X-ray crystallography, and computational quantum chemistry. The vibrational frequencies of these new molecular bui...

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Bibliographic Details
Published in:Inorganics 2019-10, Vol.7 (10), p.119
Main Authors: Hardin, April E. S., Ellington, Thomas L., Nguyen, Suong T., Rheingold, Arnold L., Tschumper, Gregory S., Watkins, Davita L., Hammer, Nathan I.
Format: Article
Language:English
Subjects:
Bonding strength
Chemical bonds
Computational chemistry
Computer applications
crystal engineering
Crystallization
Crystallography
Crystals
Density functional theory
halogen bonding
Hydrogen
Hydrogen bonding
Iodine
molecular recognition
Nitrogen
noncovalent interactions
Quantum chemistry
Raman spectroscopy
Self-assembly
sigma–hole interactions
Sulfur
supramolecular chemistry
supramolecular structures
Vibrational spectra
vibrational spectroscopy
X-ray crystallography
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Summary:Two new aromatic pyrimidine-based derivatives designed specifically for halogen bond directed self-assembly are investigated through a combination of high-resolution Raman spectroscopy, X-ray crystallography, and computational quantum chemistry. The vibrational frequencies of these new molecular building blocks, pyrimidine capped with furan (PrmF) and thiophene (PrmT), are compared to those previously assigned for pyrimidine (Prm). The modifications affect only a select few of the normal modes of Prm, most noticeably its signature ring breathing mode, ν1. Structural analyses afforded by X-ray crystallography, and computed interaction energies from density functional theory computations indicate that, although weak hydrogen bonding (C–H···O or C–H···N interactions) is present in these pyrimidine-based solid-state co-crystals, halogen bonding and π-stacking interactions play more dominant roles in driving their molecular-assembly.
ISSN:2304-6740
2304-6740
DOI:10.3390/inorganics7100119