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Article

A Structural Study of Epoxidized Natural Rubber (ENR-50) and Its Cyclic Dithiocarbonate Derivative Using NMR Spectroscopy Techniques

by
Rosniza Hamzah
1,
Mohamad Abu Bakar
1,*,
Melati Khairuddean
1,
Issam Ahmed Mohammed
2 and
Rohana Adnan
1
1
Nanoscience Research Laboratory, School of Chemical Sciences, Universiti Sains Malaysia, Penang 11800, Malaysia
2
School of Industrial Technology, Universiti Sains Malaysia, Penang 11800, Malaysia
*
Author to whom correspondence should be addressed.
Molecules 2012, 17(9), 10974-10993; https://doi.org/10.3390/molecules170910974
Submission received: 17 August 2012 / Revised: 3 September 2012 / Accepted: 3 September 2012 / Published: 12 September 2012
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Abstract

A structural study of epoxidized natural rubber (ENR-50) and its cyclic dithiocarbonate derivative was carried out using NMR spectroscopy techniques. The overlapping 1H-NMR signals of ENR-50 at δ 1.56, 1.68–1.70, 2.06, 2.15–2.17 ppm were successfully assigned. In this work, the 13C-NMR chemical shift assignments of ENR-50 were consistent to the previously reported work. A cyclic dithiocarbonate derivative of ENR-50 was synthesized from the reaction of purified ENR-50 with carbon disulfide (CS2), in the presence of 4-dimethylaminopyridine (DMAP) as catalyst at reflux temperature. The cyclic dithiocarbonate formation involved the epoxide ring opening of the ENR-50. This was followed by insertion of the C–S moiety of CS2 at the oxygen attached to the quaternary carbon and methine carbon of epoxidized isoprene unit, respectively. The bands due to the C=S and C–O were clearly observed in the FTIR spectrum while the 1H-NMR spectrum of the derivative revealed the peak attributed to the methylene protons had split. The 13C-NMR spectrum of the derivative further indicates two new carbon peaks arising from the >C=S and quaternary carbon of cyclic dithiocarbonate. All other 1H- and 13C-NMR chemical shifts of the derivative remain unchanged with respect to the ENR-50.
Keywords: ENR-50; 2D NMR; triad sequence; cyclic dithiocarbonate ENR-50; 2D NMR; triad sequence; cyclic dithiocarbonate

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MDPI and ACS Style

Hamzah, R.; Bakar, M.A.; Khairuddean, M.; Mohammed, I.A.; Adnan, R. A Structural Study of Epoxidized Natural Rubber (ENR-50) and Its Cyclic Dithiocarbonate Derivative Using NMR Spectroscopy Techniques. Molecules 2012, 17, 10974-10993. https://doi.org/10.3390/molecules170910974

AMA Style

Hamzah R, Bakar MA, Khairuddean M, Mohammed IA, Adnan R. A Structural Study of Epoxidized Natural Rubber (ENR-50) and Its Cyclic Dithiocarbonate Derivative Using NMR Spectroscopy Techniques. Molecules. 2012; 17(9):10974-10993. https://doi.org/10.3390/molecules170910974

Chicago/Turabian Style

Hamzah, Rosniza, Mohamad Abu Bakar, Melati Khairuddean, Issam Ahmed Mohammed, and Rohana Adnan. 2012. "A Structural Study of Epoxidized Natural Rubber (ENR-50) and Its Cyclic Dithiocarbonate Derivative Using NMR Spectroscopy Techniques" Molecules 17, no. 9: 10974-10993. https://doi.org/10.3390/molecules170910974

APA Style

Hamzah, R., Bakar, M. A., Khairuddean, M., Mohammed, I. A., & Adnan, R. (2012). A Structural Study of Epoxidized Natural Rubber (ENR-50) and Its Cyclic Dithiocarbonate Derivative Using NMR Spectroscopy Techniques. Molecules, 17(9), 10974-10993. https://doi.org/10.3390/molecules170910974

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