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A comprehensive study on the impact of the substituent on pKa of phenylboronic acid in aqueous and non-aqueous solutions: A computational approach
Kurnia K.A.a, Setyaningsih W.b, Darmawan N.c, Yuliarto B.d
a Department of Marine, Faculty of Fisheries and Marine, Universitas Airlangga, Kampus C Jalan Mulyorejo, Surabaya, 60115, Indonesia
b Department of Food and Agricultural Product Technology, Faculty of Agricultural Technology, Gadjah Mada University, Yogyakarta, 55281, Indonesia
c Department of Chemistry, IPB University, Bogor, 16880, Indonesia
d Department of Engineering Physics, Institut Teknologi Bandung, Bandung, 40132, Indonesia
[vc_row][vc_column][vc_row_inner][vc_column_inner][vc_separator css=”.vc_custom_1624529070653{padding-top: 30px !important;padding-bottom: 30px !important;}”][/vc_column_inner][/vc_row_inner][vc_row_inner layout=”boxed”][vc_column_inner width=”3/4″ css=”.vc_custom_1624695412187{border-right-width: 1px !important;border-right-color: #dddddd !important;border-right-style: solid !important;border-radius: 1px !important;}”][vc_empty_space][megatron_heading title=”Abstract” size=”size-sm” text_align=”text-left”][vc_column_text]© 2021 Elsevier B.V.The acid dissociation constant (pKa) is the fundamental physicochemical properties required to understand the structure and reactivity of boronic acid-based material as a sensor that identifies carbohydrates. However, there is a lack of comprehensive study on the impact of the substituent on the pKa of monosubstituted phenylboronic acid in aqueous and non-aqueous solutions. In this work, extensive experimental data on the pKa of monosubstituted phenylboronic acid in an aqueous solution was reviewed and compared in terms of accuracy. In addition, computational, were used to predict and investigate the impact of the substituent on the pKa for a series of monosubstituted phenylboronic acid in an aqueous solution at the molecular level. Good agreement was observed between predicted and literature pKa values of monosubstituted phenylboronic acid in the aqueous solution. While some deviations exist, predominantly with fluorine-containing phenylboronic acid, the COSMO-RS model is proficient at predicting the pKa of boronic acid in an aqueous solution with the accuracy of ±1.5 pKa. Subsequently, the model was used to predict the pKa of boronic acid in the non-aqueous solution, which data is not available in the literature. Furthermore, an excellent relationship is observed between the acidity of para-substituted, and to some extent, meta-substituted phenylboronic acid with the atomic charge of acidic hydrogen calculated using Natural Bond Orbital (NBO) Population Analysis. In contrast, the steric hindrance and the existence of other molecular forces might influence the acidity of ortho-substituted phenylboronic acid. The gathered information in this work could be of benefit for the understanding of the acidity of the boronic acid-based materials not only as a sensor but also in many diverse areas.[/vc_column_text][vc_empty_space][vc_separator css=”.vc_custom_1624528584150{padding-top: 25px !important;padding-bottom: 25px !important;}”][vc_empty_space][megatron_heading title=”Author keywords” size=”size-sm” text_align=”text-left”][vc_column_text]Acid dissociation constants,Computational approach,Molecular levels,Natural bond orbital,Nonaqueous solutions,Phenylboronic acids,Population analysis,Steric hindrances[/vc_column_text][vc_empty_space][vc_separator css=”.vc_custom_1624528584150{padding-top: 25px !important;padding-bottom: 25px !important;}”][vc_empty_space][megatron_heading title=”Indexed keywords” size=”size-sm” text_align=”text-left”][vc_column_text]Acidity constant,Atomic charge,Boronic acid,COSMO-RS,NBO[/vc_column_text][vc_empty_space][vc_separator css=”.vc_custom_1624528584150{padding-top: 25px !important;padding-bottom: 25px !important;}”][vc_empty_space][megatron_heading title=”Funding details” size=”size-sm” text_align=”text-left”][vc_column_text]This project is funded through Riset Kolaborasi Indonesia (RKI) 2020 between Universitas Airlangga, Universitas Gadjah Mada, Institut Pertanian Bogor, and Institut Teknologi Bandung.[/vc_column_text][vc_empty_space][vc_separator css=”.vc_custom_1624528584150{padding-top: 25px !important;padding-bottom: 25px !important;}”][vc_empty_space][megatron_heading title=”DOI” size=”size-sm” text_align=”text-left”][vc_column_text]https://doi.org/10.1016/j.molliq.2021.115321[/vc_column_text][/vc_column_inner][vc_column_inner width=”1/4″][vc_column_text]Widget Plumx[/vc_column_text][/vc_column_inner][/vc_row_inner][/vc_column][/vc_row][vc_row][vc_column][vc_separator css=”.vc_custom_1624528584150{padding-top: 25px !important;padding-bottom: 25px !important;}”][/vc_column][/vc_row]