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6939045 
Journal Article 
Isotope Effects on Hydrogen Bonding and CH/CD-pi Interaction 
Kanao, E; Kubo, T; Naito, T; Matsumoto, T; Sano, T; Yan, M; Otsuka, K; , 
2018 
Yes 
Journal of Physical Chemistry C
ISSN: 1932-7447
EISSN: 1932-7455 
AMER CHEMICAL SOC 
WASHINGTON 
15026-15032 
WOS:000438178900088 
We study the isotope effect by liquid chromatography (LC) with a variety of separation media under reversed and normal phase conditions using the protiated and/or deuterated compounds as the solutes. Results of reversed phase LC (RPLC) suggested that the protiated compounds were more hydrophobic than that of deuterated compounds due to the isotope effect based on the hydrogen bonding between hydrogen atoms of isotopologues and hydroxy groups in the mobile phase. The importance of the hydrogen bonding was also supported by the separation of isotopologues with a silica stationary phase on normal phase LC (NPLC), where the deuterated compounds showed stronger hydrogen bonding to hydroxy groups on silanol. Additionally, we investigated the difference of the strength between CH-pi and CD-pi interactions. Comparison of free energies of isotopologues by RPLC suggested that the CH -pi interaction was slightly stronger than CD-pi interaction. Finally, we demonstrated the separation of a few isotopologues on NPLC using a column coated with C-70-fullerene, which is capable of strong pi-based interactions, by effective CH/CD-pi interactions.