PMID- 37713631
OWN - NLM
STAT- PubMed-not-MEDLINE
LR  - 20231004
IS  - 1520-5215 (Electronic)
IS  - 1089-5639 (Print)
IS  - 1089-5639 (Linking)
VI  - 127
IP  - 38
DP  - 2023 Sep 28
TI  - Inductive Effects on Intramolecular Hydrogen Bond Strength: An Investigation of 
      the Effect of an Electron-Withdrawing CF(3) Group Adjacent to an Alcohol Hydrogen 
      Bond Donor.
PG  - 7892-7897
LID - 10.1021/acs.jpca.3c03485 [doi]
AB  - This combined experimental and theoretical study seeks to determine the role that 
      inductive effects have on hydrogen bonds by an investigation into the change in 
      intramolecular hydrogen bond strength in 2-amino-1-trifluoromethylethanol 
      (2ATFME) relative to that in 2-aminoethanol (2AE). Toward this end, the 
      rotational spectra of the normal, (13)C, and (15)N isotopologues have been 
      measured using Fourier transform microwave spectroscopy and fit to the 
      rotational, quadrupole coupling, and centrifugal distortion constants of the 
      Watson A-reduction Hamiltonian. Structural parameters used to characterize the 
      strength of the intramolecular hydrogen bond have been determined from the 
      experimental structures of both 2ATFME and 2AE as well as from MP2/6-311++G(d,p) 
      calculations. A comparison of these parameters in 2ATFME with those of 2AE 
      indicates that the electron-withdrawing trifluoromethyl CF(3) group strengthens 
      the hydrogen bond. These include a 4% decrease in the distance between the donor 
      and acceptor heavy atoms of the hydrogen bond, a 6% increase toward linearity of 
      the OH...N angle, and a 23% decrease of the COH...N torsional angle toward 
      planarity in 2ATFME relative to 2AE. This trend toward increased intramolecular 
      hydrogen bond strength in 2ATFME is also observed within the ab initio 
      structures.
FAU - Yap, Kaili
AU  - Yap K
AD  - Department of Chemistry and Biochemistry, College of Charleston, 66 George 
      Street, Charleston, South Carolina 29424, United States.
FAU - Krantzman, Kristin D
AU  - Krantzman KD
AD  - Department of Chemistry and Biochemistry, College of Charleston, 66 George 
      Street, Charleston, South Carolina 29424, United States.
FAU - Lavrich, Richard J
AU  - Lavrich RJ
AUID- ORCID: 0000-0003-2789-6436
AD  - Department of Chemistry and Biochemistry, College of Charleston, 66 George 
      Street, Charleston, South Carolina 29424, United States.
LA  - eng
PT  - Journal Article
DEP - 20230915
PL  - United States
TA  - J Phys Chem A
JT  - The journal of physical chemistry. A
JID - 9890903
SB  - IM
PMC - PMC10544021
COIS- The authors declare no competing financial interest.
EDAT- 2023/09/15 18:42
MHDA- 2023/09/15 18:43
PMCR- 2023/10/02
CRDT- 2023/09/15 15:34
PHST- 2023/09/15 18:43 [medline]
PHST- 2023/09/15 18:42 [pubmed]
PHST- 2023/09/15 15:34 [entrez]
PHST- 2023/10/02 00:00 [pmc-release]
AID - 10.1021/acs.jpca.3c03485 [doi]
PST - ppublish
SO  - J Phys Chem A. 2023 Sep 28;127(38):7892-7897. doi: 10.1021/acs.jpca.3c03485. Epub 
      2023 Sep 15.