Theoretical Study of Hydrogen Bond Formation in Chitosan and Pentagonal Dodecahedron Methane Hydrate Cage Structure
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1 Chem Sci Trans., 2013, 2(2), Chemical Science Transactions DOI: /cst ISSN/E-ISSN: / RESEARCH ARTICLE Theoretical Study of Hydrogen Bond Formation in Chitosan and Pentagonal Dodecahedron Methane Hydrate Cage Structure SNEHANSHU PAL and T. K. KUNDU Department of Metallurgical and Materials Engineering, Indian Institute of Technology Kharagpur, Kharagpur , India Received 19 September 2012 / Accepted 20 October 2012 Abstract: Density functional theory based calculations have been performed to study hydrogen bond formation between pentagonal dodecahedron methane hydrate cage and chitosan. The role of chitosan as a potential methane hydrate inhibitor is elucidated, based on electronic structure property correlations. Geometry optimization, frontier orbitals and natural bond orbital (NBO) analysis of methane hydrate pentagonal dodecahedron cage with and without the presence of chitosan molecule using B3LYP DFT-D/6-31++G(d,p) have been performed. Calculated interaction energies, geometrical parameters and NBO analysis reveal that chitosan has strong potential to hinder the formation of pentagonal dodecahedron methane hydrate cage. Keywords: Chitosan, Natural bond orbital, Methane hydrate inhibitor, Frontier orbital Introduction Methane hydrate is a non stoichiometric inclusion type compound belong to clathrate category and composed by hydrogen bonded cage like structure of water molecules (host) entrapping methane gas (guest) inside the cage. Methane hydrate currently become very important research topic worldwide as huge accumulations of methane hydrate in sea bed near continental margin and underneath the permafrost region of arctic are potential future energy source 1. Gas hydrate has three types of structures namely structure-i, structure-ii and structure-h 2. Density functional study of diffusion and absorption of different guest molecules in various clathrate cages 3, quantum chemical based methane accommodation study in clathrate cages 4,5, guest host interaction study of clathrate structure 6,7, IR spectroscopy analysis of vibrational form of guest molecule inside clathrate cages 8 and molecular dynamics study of nucleation of methane hydrate 9-11 have been performed. Gas hydrate formation in oil pipeline is of great concern for petroleum industry as it plugs the oil flow 12. Restriction of hydrate plug formation can be achieved through adjusting gas hydrate phase equilibrium boundary by thermodynamic inhibitors 13,14 and lingering of gas hydrate nucleation by kinetic inhibitors 13,15 and anti-agglomerates 13. Experimental study has revealed
2 448 Chem Sci Trans., 2013, 2(2), that 0.6 wt% chitosan solution is an effective kinetic inhibitor of gas hydrate 15. Theoretical analysis of chitosan and clathrate cage configuration using ab initio method has not been reported so far. Impact of presence of chitosan on the pentagonal dodecahedron hydrate cage (5 12 ) with and without entrapped methane molecule is investigated in this paper by analysing optimized structures, frontier orbital and natural bond orbital (NBO) 16,17 interaction. This work would be helpful in understanding electronic structure-property correlation based inhibition characteristics of chitosan towards methane hydrate formation. Theoretical background Interaction energy ( E ) for cluster formation has been determined using equation (1), E = E CLUSTER ECOMPONENTS (1) Where, E CLUSTER and E COMPONENTS are optimized energy of cluster and individual components respectively. A structure is more stable if its interaction energy is more negative compared to other configurations. In case of NBO analysis, donor-acceptor interplay strength between filled orbital of the donor ( φ ) and the empty orbital of acceptor ( φ ) has (2) been estimated by calculation of second order perturbation energy ( E ij ) using equation (2), < φi F φ j > (2) Eij = 2 (2) ε i ε j Where, ε and i i ε j are NBO energies, F is Fock matrix element between the i and j NBO orbitals. NBO analysis helps to understand intra and intermolecular interactions by providing details of interplays in filled as well as virtual orbital. It is well known method for analysing hyper conjugative interactions 18. Simulation details Geometry optimization of methane encapsulated pentagonal dodecahedron (1CH 12 ) and chitosan system have been performed by density functional theory using B3LYP DFT-D /6-31++G(d,p) method. B3LYP DFT-D functional incorporates the dispersion energy with Kohn-Sham density-functional theory 22,23 and uses unscaled correction of dispersion term. B3LYP functional with DFT-D term is good choice for density functional theory calculation of the hydrate clathrate system studied here, having van der Waals interactions. NBO analysis has been performed at B3LYP DFT-D /6-31++G(d,p) level of theory. All the simulations have been carried out by using Gaussian 09 software package 24. Visualization of molecules have been carried out in discovery studio v3.1 of Accelrys Software Inc. Results and Discussion Optimized structure of 5 12 cage, chitosan complex, 1CH 12 cage and 1CH 12 + chitosan complex are shown in Figure 1(a), Figure 1(b), Figure 2(a) and Figure 2(b) respectively. It is observed that three intermolecular hydrogen bonds between chitosan and 5 12 cage are formed in both chitosan complex (O14-H25...N90, O111-H112...O15 and O9-H21...O82) and 1CH 12 -chitosan complex (O14-H25...N95, O116-H117...O15 and O9-H21...O87). The average and range of O-H bond length, hydrogen bond distance and hydrogen bond angle (O-H...O) of 5 12 cage and 1CH 12 cage with and without presence of chitosan are summarized in Table 1. The range of hydrogen bond distance and hydrogen j
3 Chem Sci Trans., 2013, 2(2), bond angle are found to be expanded in presence of chitosan for the both 5 12 cage and 1CH 12 cage. Standard deviation from average hydrogen bond distance and hydrogen bond angle become higher in presence of chitosan for both 5 12 cage and 1CH 12 cage, as evident in Table 1. (a) (b) Figure 1. Optimized structures using B3LYP DFT-D/6-31++G(d,p) of (a) Empty 5 12 Cage (b) Chitosan + empty 5 12 Cage (colour legend : red = oxygen, black = carbon, blue = nitrogen and whitish grey = hydrogen and black dotted line is hydrogen bond) [see online for colour figure]
4 450 Chem Sci Trans., 2013, 2(2), (a) (b) Figure 2. Optimized structures using B3LYP DFT-D/6-31++G(d,p) of (a) 1CH 12 Cage (b) Chitosan + 1CH 12 Cage (colour legend : red = oxygen, black = carbon, blue = nitrogen and whitish grey = hydrogen and black dotted line is hydrogen) [see online for colour figure]
5 Chem Sci Trans., 2013, 2(2), Table 1. Calculated average O-H bond length (Å), Hydrogen bond distance (Å) and Hydrogen bond Angle ( ) along with their ranges using B3LYP DFT-D/ G (d, p) (Standard deviation is given in parenthesis) Systems O-H bond length(å) H-bond Distance(Å) H-bonded Angle ( ) Range Avg. Range Avg. Range Avg Empty (0.01) (0.05) (2.67) 1CH (0.01) (0.03) (3.00) Chitosan (0.01) Empty (0.15) (10.69) Chitosan CH (0.01) (0.15) (10.72) It can be inferred that some distortions of both 5 12 cage and 1CH 12 cage occurred in presence of chitosan. It is also identified that interaction energies ( E) for hydrogen bonded 5 12 cage + chitosan complex and 1CH 12 cage + chitosan complex are much less compared to that of both 5 12 cage and 1CH 12 cage, as shown in Table 2. It is obvious that distortion of 5 12 cage and 1CH 12 cage in presence of chitosan is very likely due to hydrogen bond interaction between chitosan and 5 12 cage or 1CH 12 cage. Table 2. Calculated interaction energy ( E, kcal/mole) for different cluster using B3LYP DFT-D functional and G (d, p) basis set Systems E 5 12 Empty CH 12 cage Chitosan Empty Chitosan + 1CH 12 cage Highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) of chitosan, 5 12 cage, chitosan complex, 1CH 12 cage and 1CH 12 + chitosan complex are presented in Figure 2. The HOMO of chitosan complex originates essentially from the HOMO of chitosan with negligible contribution of anti bonding orbital of 5 12 cage, but the LUMO of the same complex arises largely from the LUMO of 5 12 cage. Similarly, HOMO of 1CH 12 cage + chitosan complex originates essentially from the HOMO of chitosan with negligible contribution of anti bonding orbital of 1CH 12 cage, but the LUMO of the same complex arises largely from the LUMO of 1CH 12 cage. It can be inferred that intermolecular hydrogen bonds between chitosan and 5 12 cage or 1CH 12 cage has strong covalent character. a
6 452 Chem Sci Trans., 2013, 2(2), b c d e Figure 3. Frontier orbitals of (a) Chitosan; (b) Empty 5 12 Cage; (c) Chitosan + empty 5 12 Cage; (d) 1CH 12 Cage; (e) Chitosan + 1CH 12 Cage by B3LYP DFT-D/6-31++G(d,p) theory (colour legend : red = oxygen, black = carbon, blue = nitrogen and whitish grey = hydrogen. For colour version see online article). The calculated second order perturbation energies of some selective donor and acceptor interaction from NBO analysis using B3LYP DFT-D /6-31++G(d,p) are shown in Table 3. The presence of donor acceptor interplays are obvious from the calculated second order perturbation energy values of 5 12 cage + chitosan complex and 1CH 12 cage + chitosan configurations. Three intermolecular hydrogen bonds between chitosan and 5 12 cage are formed in both chitosan complex (O14-H25...N90, O111-H112...O15 and O9-H21...O82) and 1CH 12 -chitosan complex (O14-H25...N95, O116-H117...O15 and O9-H21...O87)
7 Chem Sci Trans., 2013, 2(2), have strong donor acceptor interactions as high second order perturbation energies for those hydrogen bonds are found in Table 3. This tendency of formation strong hydrogen bond between chitosan and water molecule of 5 12 cluster would provide hindrance to the methane hydrate formation in presence of chitosan. ( 2) Table 3. Calculated second order perturbation energy (, kcal/mole) for chitosan and chitosan + 1CH 12 using B3LYP DFT-D/6-31++G (d, p) System Donor Acceptor Chitosan Cage Chitosan + 1CH 12 cage LP(1)O9 BD * (1)O19-H LP(2)O19 BD * (1)O15-H LP(1)O14 BD * (1)O15-H LP(2)O14 BD * (1)O11-H LP(2)O9 BD * (1)O11-H LP(2)O82 BD * (1)O9-H LP(1)O15 BD * (1)O111-H LP(1)N90 BD * (1)O14-H LP(2)O9 BD * (1)O19-H LP(2)O19 BD * (1)O15-H LP(2)O14 BD * (1)O15-H LP(2)O14 BD * (1)O11-H LP(2)O9 BD * (1)O11-H LP(2)O87 BD * (1)O9-H LP(1)O15 BD * (1)O116-H LP(1)N95 BD * (1)O14-H Conclusion Scientific explanation for the role of chitosan as methane hydrate inhibitor have been reported using first principle based calculation. Calculated interaction energies, geometrical parameters, frontier orbitals and NBO analysis reveal that chitosan has strong potential to form strong hydrogen bonds with water molecules of 1CH 12 cage and consequently hinder its formation. This study will help to visualize the inherent scientific logic behind the role of chitosan as inhibitor for methane hydrate and the conspectus of this study can be extended to explain potential of different gas hydrate inhibitors using electronic structure property correlation based concept. Acknowledgment This work is financially supported by Ministry of Earth Science, Govt. of India (Project No. MoES/16/48/09-RDEAS (MRDM5)). We thank Accelrys Inc. for providing free Discovery studio 3.1 visualization tool. References 1. Collet T S, AAPG Bulletin, 2002, 86(11), Sloan Jr E D, Nature, 2003, 426, Román-Pérez G, Moaied M, Soler J M and Yndurain F, Phy Rev Lett., 2010, 105, Pal S and Kundu T K, J Petro Eng Tech., 2012, 2, Pal S and Kundu T K, J Petro Eng Tech., 2012, 2, E ij E ij ( 2)
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