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Structure of 4-[4-(Dimethylamino)-Phenylazo] Benzeneboronic Acid and Its Cyclic Esters with D-Glucose: A Computational Study

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Abstract

We present results from a computational study of 4-[4-(dimethylamino)-phenylazo] benzene boronic acid (DABBA) (the 4'-boronic acid isomer of the aminoazobenzene dye N,N-dimethylaminoazobenzene) and its associated anion, as well as, several cyclic esters formed from these azoborates and various conformers of D-glucose. Azo dyes that also contain one or more boronic acid functional groups are of practical importance in the development of chemical sensors for saccharide recognition because of their ability to induce a visible color change upon binding. The lowest-energy DABBA:D-glucose esters found in this investigation consistently involved at least one of the exocyclic hydroxymethyl groups on the D-glucose moiety rather than vicinal cis or trans diol arrangements of hydroxyl groups on the ring.

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  1. Department of Chemistry and Biochemistry, School of Science and Health, Philadelphia University, School House Lane and Henry Avenue, Philadelphia, Pennsylvania, 19144

    Seth Hayik, Krishna L. Bhat & Charles W. Bock

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  1. Seth Hayik
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  2. Krishna L. Bhat
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  3. Charles W. Bock
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Correspondence to Charles W. Bock.

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Hayik, S., Bhat, K.L. & Bock, C.W. Structure of 4-[4-(Dimethylamino)-Phenylazo] Benzeneboronic Acid and Its Cyclic Esters with D-Glucose: A Computational Study. Structural Chemistry 15, 133–147 (2004). https://doi.org/10.1023/B:STUC.0000011248.28922.3b

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