Multiple Hydrogen Bond Tethers for Grazing Formic Acid in Its Complexes
with Phenylacetylene
Version 4 2018-02-13, 18:36
Version 3 2018-02-12, 20:34
Version 2 2018-02-08, 20:02
Version 1 2018-02-08, 19:58
Posted on 2018-02-13 - 18:36
Complexes
of phenylacetylene (PhAc) and formic acid (FA) present an interesting
picture, where the two submolecules are tethered, sometimes multiply,
by hydrogen bonds. The multiple tentacles adopted by PhAc–FA
complexes stem from the fact that both submolecules can, in the same
complex, serve as proton acceptors and/or proton donors. The acetylenic
and phenyl π systems of PhAc can serve as proton acceptors,
while the C–H or −C–H of the phenyl ring
can act as a proton donor. Likewise, FA also is amphiprotic. Hence,
more than 10 hydrogen-bonded structures, involving O–H···π,
C–H···π, and C–H···O
contacts, were indicated by our computations, some with multiple tentacles.
Interestingly, despite the multiple contacts in the complexes, the
barrier between some of the structures is small, and hence, FA grazes
around PhAc, even while being tethered to it, with hydrogen bonds.
We used matrix isolation infrared spectroscopy to experimentally study
the PhAc–FA complexes, with which we located global and a few
local minima, involving primarily an O–H···π
interaction. Experiments were corroborated by ab initio computations,
which were performed using MP2 and M06-2X methods, with 6-311++G (d,p)
and aug-cc-pVDZ basis sets. Single-point energy calculations were
also done at MP2/CBS and CCSD(T)/CBS levels. The nature, strength,
and origin of these noncovalent interactions were studied using AIM,
NBO, and LMO-EDA analysis.
CITE THIS COLLECTION
DataCite
3 Biotech
3D Printing in Medicine
3D Research
3D-Printed Materials and Systems
4OR
AAPG Bulletin
AAPS Open
AAPS PharmSciTech
Abhandlungen aus dem Mathematischen Seminar der Universität Hamburg
ABI Technik (German)
Academic Medicine
Academic Pediatrics
Academic Psychiatry
Academic Questions
Academy of Management Discoveries
Academy of Management Journal
Academy of Management Learning and Education
Academy of Management Perspectives
Academy of Management Proceedings
Academy of Management Review
Karir, Ginny; Kumar, Gaurav; Kar, Bishnu Prasad; Viswanathan, K. S. (2018). Multiple Hydrogen Bond Tethers for Grazing Formic Acid in Its Complexes
with Phenylacetylene. ACS Publications. Collection. https://doi.org/10.1021/acs.jpca.7b11428
or
Select your citation style and then place your mouse over the citation text to select it.
SHARE
Usage metrics
Read the peer-reviewed publication
AUTHORS (4)
GK
Ginny Karir
GK
Gaurav Kumar
BK
Bishnu Prasad Kar
KV
K. S. Viswanathan