Quantum mechanical modeling of the structures, energetics and spectral properties of Iα and Iβ cellulose

Cellulose

Volumn 20, Issue 1, 2013, Pages 9-23

  Kubicki, James D ^a   Mohamed, Mohamed Naseer Ali ^b   Watts, Heath D ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

^b VIT UNIVERSITY   (India)

Author keywords

Cellulose; DFT; Infrared; NMR; Raman

Indexed keywords

CHEMICAL BONDS; CONFORMATIONS; DENSITY FUNCTIONAL THEORY; INFRARED RADIATION; NEUTRON DIFFRACTION; NUCLEAR MAGNETIC RESONANCE; QUANTUM THEORY;

DISPERSION CORRECTION; HYDROXYMETHYL GROUPS; NUCLEAR MAGNETIC RESONANCE CHEMICAL SHIFTS; PERIODIC DFT CALCULATION; QUANTUM MECHANICAL MODEL; RAMAN; SPECTRAL PROPERTIES; X-RAY AND NEUTRON DIFFRACTION;

CELLULOSE;

EID: 84872323106     PISSN: 09690239     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10570-012-9838-6     Document Type: Article

References (64)

1. Agarwal UP, Reiner RS, Ralph SA (2010) Cellulose I crystallinity determination using FT-Raman spectroscopy: univariate and multivariate methods. Cellulose 17(4): 721-733.
2. Atalla R (1999) Carbohydrates and their derivatives including tannins, cellulose and related lignins. In: Barton D, Nakanishi K (eds) Comprehensive natural products chemistry, 3rd edn. Elsevier, Amsterdam, pp 529-598.
3. Atalla R, VanderHart D (1984) Native cellulose: a composite of two distinct crystalline forms. Science 223: 283-285.
4. Blackwell J (1977) Infrared and Raman spectroscopy of cellulose. In: Aurthur J (ed) Cellulose chemistry and technology, ACS symposium series. American Chemical Society, Washington, DC, pp 206-218.
5. Bućko T, Tunega D, Ángyán JG, Hafner J (2011) Ab initio study of structure and interconversion of native cellulose phases. J Phys Chem A 115: 10097-10105.
6. Chai J-D, Head-Gordon M (2008) Long-range corrected hybrid density functionals with damped atom-atom dispersion corrections. Phys Chem Chem Phys 10(44): 6615-6620.
7. Cheeseman JR, Trucks GW, Keith TA, Frisch MJ (1996) A comparison of models for calculating nuclear magnetic resonance shielding tensors. J Chem Phys 104(14): 5497-5509.
8. Cirtog M, Alikhani ME, Madebène B, Soulard P, Asselin P, Tremblay B (2011) Bonding nature and vibrational signatures of oxirane: (water) n = 1-3. Assessment of the performance of the dispersion-corrected DFT methods compared to the ab initio results and Fourier transform infrared experimental data. J Phys Chem A 115(24): 6688-6701.
9. Earl WL, VanderHart DL (1981) Observations by high-resolution carbon-13 nuclear magnetic resonance of cellulose i related to morphology and crystal structure. Macromolecules 14: 570-574.
10. Earl WL, VanderHart DL (1984) Studies of microstructure in native celluloses using solid-state carbon-13 NMR. Macromolecules 17(8): 1465-1472.
11. Eck B (2012) wxDragon. Retrieved from www. wxdragon. de.
12. 13C labeled glucose. Cellul Commun 4: 128-131.
13. Fernandes AN, Thomas LH, Altaner CM, Callow P, Forsyth VT, Apperely DC, Kennedy CJ et al (2011) Nanostructure of cellulose microfibrils in spruce wood. Proc Natl Acad Sci USA 108(47): E1195-E1203.
14. Fiadzomor PAY, Keen AM, Grant RB, Orr-Ewing AJ (2008) Interaction energy of water dimers from pressure broadening of near-IR absorption lines. Chem Phys Lett 462(4-6): 188-191.
15. French AD, Johnson GP (2009) Cellulose and the twofold screw axis: modeling and experimental arguments. Cellulose 16(6): 959-973.
16. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr et al (2009) Gaussian 09 Revision B. 01. Gaussian, Inc, Wallingford, CT.
17. Gonzalez-Outeiriño J, Kirschner KN, Thobhani S, Woods RJ (2006) Reconciling solvent effects on rotamer populations in carbohydrates-a joint MD and NMR analysis. Can J Chem 84(4): 569-579.
18. Grimme S (2006) Semiempirical GGA-type density functional constructed with a long-range dispersion correction. J Comput Chem 27(15): 1787-1799.
19. n with n = 2 - 6 recorded with a time-of-flight mass spectrometer using infrared depletion and vacuum-ultraviolet ionization. J Chem Phys 134(14): 144309-144319.
20. Hanus J, Mazeau K (2006) The xyloglucan-cellulose assembly at the atomic scale. Biopolymers 82: 59-73.
21. Harris DM, Corbin K, Wang T, Gutierrez R, Bertolo AL, Carloalberto P, Smilgies D-M et al (2012) Cellulose microfibril crystallinity is reduced by mutating C-terminal transmembrane region residues CESA1A903 V and CESA3T942I of cellulose synthase. Proc Natl Acad Sci USA 109(11): 4098-4103.
22. Heiner AP, Sugiyama J, Teleman O (1995) Crystalline cellulose Iα and Iβ studied by molecular-dynamics simulation. Carbohydr Res 273(2): 207-223.
23. 13C-labeled bacterial celluloses of different Gluconacetobacter xylinus strains. Magn Reson Chem 46: 1030-1036.
24. Himmel ME, Ruth MF, Wyman CE (1999) Cellulase for commodity products from cellulosic biomass. Curr Opin Biotechnol 10: 358-364.
25. Himmel ME, Di S-Y, Johnson DK, Adney WS, Nimlos MR, Brady JW, Foust TD (2007) Biomass recalcitrance: engineering plants and enzymes for biofuels. Science 315: 804-807.
26. Huisken F, Kaloudis M, Kulcke A (1996) Infrared spectroscopy of small size-selected water clusters. J Chem Phys 104(17): 17-25.
27. Kim H, Choi J, Goddard WA (2012) Universal correction of density functional theory to include London dispersion (up to Lr, element 103). J Phys Chem Lett 3(3): 360-363.
28. Koch F-T, Priess W, Witter R, Sternberg U (2000) Calculation of solid-state 13C NMR spectra of cellulose Iα, Iβ and II using a semi-empirical approach and molecular dynamics. Macromol Chem Phys 201(15): 1930-1939.
29. Kresse G, Furthmüller J (1996) Efficient iterative schemes for ab initio total-energy calculations using a plane-wave basis set. Phys Rev B 54: 11169-11186.
30. Kresse G, Hafner J (1993) Ab initio molecular dynamics for open-shell transition metals. Phys Rev B 48(17): 13115-13118.
31. Kresse G, Hafner J (1994) Ab initio molecular-dynamics simulation of the liquid-metal-amorphous-semiconductor transition in germanium. Phys Rev B 49(20): 14251-14269.
32. Kresse G, Furthmüller J, Hafner J (1994) Theory of the crystal structures of selenium and tellurium: the effect of generalized-gradient corrections to the local-density approximation. Phys Rev B 50(18): 13181-13185.
33. Lee CM, Park YB, Mohamed MNA, Kubicki JD, Roberts E, Cosgrove et al (2012) Structural understanding of cellulose from sum-frequency-generation (SFG) spectroscopy analyses. In: 243rd American chemical society national meeting and exposition. American Chemical Society, San Diego.
34. Li Y, Lin M, Davenport JW (2011) Ab Initio studies of cellulose I: crystal structure, intermolecular forces, and interactions with water. J Phys Chem C 115(23): 11533-11539.
35. Lovas F, Belov S, Tretyakov M, Stahl W, Suenram RD (1995) The a-Type K = 0 microwave spectrum of the methanol dimer. J Mol Spectrosc 170: 478-492. Retrieved from http://www. sciencedirect. com/science/article/pii/S0022285285710867.
36. Lynd LR, Cushman JH, Nichols RJ, Wyman CE (1991) Fuel ethanol from cellulosic biomass. Science 251: 1318-1323.
37. Maréchal Y, Chanzy H (2000) The hydrogen bond network in Iβ cellulose as observed by infrared spectrometry. J Mol Struct 523(1-3): 183-196.
38. Matthews JF, Skopec CE, Mason PE, Zuccato P, Torget RW, Sugiyama J, Himmel ME et al (2006) Computer simulation studies of microcrystalline cellulose Iβ. Carbohydr Res 341: 138-152.
39. Matthews JF, Beckham GT, Bergenstråhle-Wohlert M, Brady JW, Himmel ME, Crowley MF (2012) Comparison of cellulose Iβ simulations with three carbohydrate force fields. J Chem Theory Comput 8(2): 735-748.
40. Mazeau K, Charlier L (2012) The molecular basis of the adsorption of xylans on cellulose surface. Cellulose 19(2): 337-349.
41. Moon RJ, Martini A, Nairn J, Simonsen J, Youngblood J (2011) Cellulose nanomaterials review: structure, properties and nanocomposites. Chem Soc Rev 40(7): 3941-3994.
42. Newman RH, Davidson TC (2004) Molecular conformations at the cellulose-water interface. Cellulose 11: 23-32.
43. Nishiyama Y, Langan P, Chanzy H (2002) Crystal structure and hydrogen-bonding system in cellulose Iβ from synchrotron X-ray and neutron fiber diffraction. J Am Chem Soc 124(31): 9074-9082.
44. Nishiyama Y, Sugiyama J, Chanzy H, Langan P (2003) Crystal structure and hydrogen bonding system in cellulose Iα from synchrotron X-ray and neutron fiber diffraction. J Am Chem Soc 125(47): 14300-14306.
45. Nishiyama Y, Johnson GP, French AD, Forsyth V, Langan P (2008) Neutron crystallography, molecular dynamics, and quantum mechanics studies of the nature of hydrogen bonding in cellulose Iβ. Biomacromolecules 9(11): 3133-3140.
46. O'Sullivan AC (1997) Cellulose: the structure slowly unravels. Cellulose 4(3): 173-207.
47. Odutola JA, Dyke TR (1980) Partially deuterated water dimers: microwave spectra and structure. J Chem Phys 72(9): 5062-5070.
48. Payen A (1838) Memoir on the composition of the tissue of plants and of woody material. CR Biol 7: 1052-1056.
49. Rassolov VA, Ratner MA, Pople JA, Redfern PC, Curtiss LA (2001) 6-31G* basis set for third-row atoms. J Comput Chem 22: 976-984.
50. 2, by velocity map imaging. J Chem Phys 134(21): 211101-211104.
51. Sarotti AM, Pellegrinet SC (2009) A multi-standard approach for GIAO (13)C NMR calculations. J Org Chem 74(19): 7254-7260.
52. 13C chemical shifts. Cellulose 10: 189-199.
53. Štrucova A, His I, Apperley DC, Sugiyama J, Jarvis MC (2004) Structural details of crystalline cellulose from higher plants. Biomacromolecules 5: 1333-1339.
54. Suzuki S, Horiia F, Kurosu H (2009) Theoretical investigations of 13C chemical shifts in glucose, cellobiose, and native cellulose by quantum chemistry calculations. J Mol Struct 921(1-3): 219-226.
55. Tavagnacco L, Masona PE, Schnupfa U, Piticia F, Zhong L, Himmel ME, Crowley M et al (2011) Sugar-binding sites on the surface of the carbohydrate-binding module of CBH I from Trichoderma reesei. Carbohydr Res 346(6): 839-846.
56. Tormo J, Lamed R, Chirino AJ, Morag E, Bayer EA, Shoham Y, Steitz TA (1996) Crystal structure of a bacterial family-III cellulose-binding domain: a general mechanism for attachment to cellulose. J Eur Mol Biol Organ (EMBO) 5: 5739-5751.
57. Viëtor RJ, Newman RH, Ha M-A, Apperely DC, Jarvis MC (2002) Conformational features of crystal-surface cellulose from higher plants. Plant J 30: 721-731.
58. Watts HD, Mohamed MNA, Kubicki JD (2011) Comparison of multistandard and TMS-standard calculated NMR shifts for coniferyl alcohol and application of the multistandard method to lignin dimers. J Phys Chem B 115(9): 1958-1970.
59. Wiley JH, Atalla, RA (1987) Band assignments in the Raman spectra of celluloses. Carbohydr Res 160: 113-129.
60. Witter R, Sternberg U, Hesse S, Kondo T, Koch F-T, Ulrich AS (2006) 13C chemical shift constrained crystal structure refinement of cellulose Iα and its verification by NMR anisotropy experiments. Macromolecules 38(19): 6125-6132.
61. Wolinski K, Hinton JF, Pulay P (1990) Efficient implementation of the gauge-independent atomic orbital method for NMR chemical shift calculations. J Am Chem Soc 112: 8251-8260.
62. Xie H, Pincu M, Brauer B, Gerber RB (2011) Raman and infrared spectra of cellobiose in the solid state: what can be learned from single-molecule calculations? Chem Phys Lett 514: 284-290.
63. Zhao Y, Schultz NE, Truhlar DG (2006) Design of density functionals by combining the method of constraint satisfaction with parametrization for thermochemistry, thermochemical kinetics, and noncovalent interactions. Design 2: 364-382.
64. Zhong L, Matthews JF, Crowley MF, Rignall T, Talón C, Cleary JM, Walker RC et al (2008) Interactions of the complete cellobiohydrolase I from Trichodera reesei with microcrystalline cellulose Iβ. Cellulose 15(2): 261-273.