[논문]Hydrogen Bonding in Aromatic Alcohol-Water Clusters: A Brief Review

Ahn, Doo-Sik; Jeon, In-Sun; Jang, Sang-Hee; Park, Sung-Woo; Lee, Sung-Yul; Cheong, Won-Jo

doi:10.5012/bkcs.2003.24.6.695

Hydrogen Bonding in Aromatic Alcohol-Water Clusters: A Brief Review 원문보기

Bulletin of the Korean chemical society, v.24 no.6, 2003년, pp.695 - 702

Ahn, Doo-Sik (경희대학교) , Jeon, In-Sun (경희대학교) , Jang, Sang-Hee (경희대학교) , Park, Sung-Woo (경희대학교) , Lee, Sung-Yul (경희대학교) , Cheong, Won-Jo (인하대학교)

Abstract ▼ AI-Helper

Recent experimental and theoretical advances on the aromatic alcohol-water clusters are reviewed, focusing on the structure of the hydrogen bonding between the alcoholic OH group and the binding water molecules. The interplay of experimental observations and theoretical calculations for the elucidation of the structure is demonstrated for phenol-water, benzyl alcohol-water, substituted phenol-water, naphthol-water and tropolone -water clusters. Discussion is made on assigning the role (either proton-donating or -accepting) of the hydroxyl group by measuring the shifts of infrared frequency of the OH stretching mode in the cluster from that of bare aromatic alcohol for the experimental determination of the cluster structure.

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가설 설정

Since the alcoholic hydroxyl group lies almost in the phenyl ring, the four-membered ring lies beyond the phenyl ring. The isomer of the benzyl alcohol-(H₂O)₃ cluster of the lowest energy is (B31) shown in Figure 4. In this isomer the three water molecules and the hydroxyl group form a ring. Since the ring lies away from the phenyl ring, π bond cannot be formed between water and the phenyl ring in this isomer.
cluster is well-known and has been studied by many groups. In this structure (P31) the four oxygen atoms form a ring as shown in Figure 4. Since the alcoholic hydroxyl group lies almost in the phenyl ring, the four-membered ring lies beyond the phenyl ring. The isomer of the benzyl alcohol-(H₂O)₃ cluster of the lowest energy is (B31) shown in Figure 4.

제안 방법

The β-Naphthol-(H₂O)_n (n =1-3,5) clusters were investigated by Mikami and coworkers37 both experimentally and computationally. By employing the IR-UV double resonance technique, they observed the hydrogen-bonded OH stretching frequencies, and assigned the structures of the clusters by comparing with the ab initio calculations. As in the case of p-cresol-water clusters discussed above, the (0,0) band of β-Naphthol- (H₂O)₁ shifts to red from that of bare Q-Naphthol, while those of the clusters with n > 2 blue shift with respect to that of the n = 1 cluster.
For the electron-donating groups, the reverse trend was predicted. They carried out calculations (by employing the MP2/6-311G ** method) for -F and -Cl (-NH₂ and -OH) as electron-withdrawing (-donating) substituents, and found that their predictions are indeed correct. The changes in the binding energies due to the substituents were calculated to be about 0.
They found that the (0,0) band ofthe π- π transitions of the p-cresol-(H₂O)_1·3 cluster significantly (by 357 cm^-1) red shifts from that of the bare cresol, while those of the pcresol-(H₂O)_2·3 clustersred shift to a lesser degree (107 and 76 cm^-1, respectively). They explained this behavior of the electronic spectra by carrying out the ab initio calculations for the HOMO-LUMO gap for the π- π transitions, and by analyzing the effects of proton-accepting or -donating water molecule(s) on the HOMO and LUMO of the clusters, in good agreement with the experimental observations. They also found that the intermolecular stretching frequency (185cm^-1) of p-cresol-(H₂O)₃ is significantly higher than that (146 cm^-1) of p-cresol-(H₂O)₃, and attributed this observation to the more rigid O-O potential of the cyclic water trimer in p-cresol-(H₂O)₃ cluster.

성능/효과

The calculated infrared frequencies also exhibited very interesting pattern: It was found that the harmonic frequency of the stretching mode of the proton-donating OH group in the substituted phenol moiety in the complexes significantly decrease from that of bare substituted phenol (for example, while the OH stretching mode frequency of the p-fluorophenol is computed to be 3886 cm^-1, that of the corresponding complex p-FP11 is calculated to be only 3706 cm^-1), and that the harmonic frequency of the stretching mode of the proton-accepting OH group in the substituted phenol moiety in the complexes remained more or less the same as that of bare substituted phenol (for example, the harmonic frequency of the p-fluorophenol-water complex p-FP12, which possess proton-accepting phenolic OH group, is computed to be 3888 cm^-1, while that of bare p-fluorophenol is computed to be 3886 cm^-1). This latter observation may help elucidate the structures of the substituted phenol-water complexes by the infrared spectroscopic methods, determining whether the phenolic OH group is proton-donating or -accepting.

후속연구

By observing that the IR spectra for the tropolone- (H₂O)₁ cluster exhibited two distinct band for the two OH stretching modes of the water moiety, the two groups proposed TP11 and TP12 (Figure 15) as the probable structures for the tropolone-(H₂O)₁ cluster. Preference of the two groups differed (for example, Mikami and co-workers³⁸ preferred the structure TP11 on the basis of several spectroscopic arguments and by comparing the IR spectra for the tropolone- (CH₃OH)₁ cluster, while Zwier and co-workers³⁹ expressed slight preference for TP12), however, and further detailed analysis would be needed for unambiguous elucidation of the structure. For the tropolone-(H₂O)₂ cluster, Mikami and co-workers proposed TP21 and TP22 as the two most probable structures, but definite assignment was not made.

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