Malaysian Journal of Analytical Sciences Vol 23 No 2 (2019): 182 - 188

DOI: 10.17576/mjas-2019-2302-01

 

 

 

DETERMINATION OF BINDING CONSTANT OF MOLECULAR COMPLEX BETWEEN β-CYCLODEXTRIN AND BISPHENOL A BY USING ¹H NMR SPECTROSCOPY

 

(Penentuan Malar Penambatan Kompleks Molekul di antara β-siklodekstrin dan Bisfenol A Menggunakan Spektroskopi ¹H NMR)

 

Rosliana Rusli, Mohd Bakri Bakar*, Salasiah Endud, Zainab Ramli

 

Department of Chemistry, Faculty of Science,

Universiti Teknologi Malaysia, 81310 UTM Johor Bahru, Johor, Malaysia

 

*Corresponding author:  bakribakar@utm.my

 

 

Received: 4 July 2018; Accepted: 24 January 2019

 

 

Abstract

The inclusion complexation behaviour of bisphenol A (BPA) into hydrophobic cavity of β-cyclodextrin (β-CD) was investigated by using ¹H NMR spectroscopy in deuterium oxide by varying the molar ratios between β-CD and BPA from 1:0 to 1:2. The ideal molar ratio for the β-CD:BPA complex was determined as 1:1. In addition, the inclusion of BPA into β-CD produced significant changes in the chemical shifts of H5 and H3 protons, which were located inside the cavity of cyclodextrin. On the other hand, the H2, H4 and H6 protons that were located at the exterior surface of β-CD did not result in any significant changes in the chemical shift, and thus confirmed the formation of the β-CD:BPA inclusion complex. The observed chemical shifts of H5 and H3 protons, when BPA interacted with the β-CD cavity, were utilised to determine the binding association constant  (K_a) and maximum chemical shift difference (∆_max). From the nonlinear calculation, the K_a for H3 proton, i.e. 4.10 x 10³ M^-1, was shown to be stronger than that of H5, i.e. 3.62 x 10³ M^-1. However, the H5 proton gave a higher ∆_max than the H3 proton, which were 0.1412 ppm and 0.0573 ppm, respectively.

 

Keywords:  cyclodextrin, bisphenol A, binding association constant

 

Abstrak

Kelakuan pengkompleksan rangkuman oleh bisfenol A (BPA) ke dalam rongga hidrofobik β-siklodekstrin (β-CD) diselidik melalui penggunaan spektroskopi ¹H NMR dalam deuterium oksida dengan mengubah nisbah molar antara β-CD dan BPA dari 1:0 hingga 1:2. Nisbah molar yang unggul untuk kompleks β-CD:BPA ditentukan sebagai 1:1. Tambahan pula, rangkuman BPA ke dalam β-CD menyebabkan perubahan ketara terhadap anjakan kimia pada proton H5 dan H3 siklodekstrin yang terletak di dalam rongga. Selain itu, proton H2, H4 dan H6 yang terletak di luar permukaan β-CD tidak mengalami perubahan pada anjakan kimia, dengan ini membuktikan bahawa pembentukan kompleks rangkuman β-CD:BPA. Perubahan anjakan kimia yang diperhatikan daripada proton H5 and H3 apabila BPA saling bertindak dengan rongga β-CD, digunakan untuk menentukan malar penyekutuan penambatan (K_a) dan perubahan anjakan kimia maksimum (∆_max). Menggunakan hitungan tak-linear, malar K_a untuk proton H3 ialah 4.10 x 10³ M^-1 dilihat lebih kuat berbanding dengan proton H5, iaitu 3.62 x 10³      M^-1. Walau bagaimanapun, proton H5 memberikan ∆_max yang ketara, iaitu 0.1412 ppm berbanding dengan proton H3, iaitu 0.0573 ppm.

 

Kata kunci:  siklodekstrin, bisfenol A, pemalar penyekutuan penambatan

 

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