Crystal Structure Models for the Aldaramide Units of Poly(pentaramides)

REFERENCES

• Ogata , N. and Okamoto , S. 1973 . Synthesis of polyesters from active diesters . J. Polym. Sci. Part A: Polym. Chem. , 11 : 2537 – 2545 .
   Web of Science ®Google Scholar
• Ogata , N. and Hosoda , Y. 1974 . Synthesis of hydrophilic polyamide by active polycondensation . J. Polym. Sci. Polym. Lett. , 12 : 355 – 358 .
   Web of Science ®Google Scholar
• Ogata , N. and Hosoda , Y. 1975 . Synthesis of hydrophilic polyamide from l-tartarate and diamines by active polycondensation . J. Polym. Sci. Part A: Polym. Chem , 13 : 1793 – 1801 .
   Web of Science ®Google Scholar
• Ogata , N. , Sanui , K. , Hosoda , Y. and Nakamura , H. 1976 . Active polycondensation of diethyl 2,3,4,5-tetrahydroxyadipate with diamines . J. Polym. Sci. Part A: Polym. Chem. , 14 : 783 – 792 .
   Web of Science ®Google Scholar
• Ogata , N. and Sanui , K. 1977 . Copolymerization of hydroxyl diesters and active diesters with hexamethylenediamine . J. Polym. Sci. Part A: Polym. Chem. , 15 : 1523 – 1526 .
   Web of Science ®Google Scholar
• Hoagland , P. D. 1981 . The formation of intermediate lactones during aminolysis of diethyl galactarate . Carbohydr. Res. , 98 : 203 – 208 .
   Web of Science ®Google Scholar
• Hoagland , P. D. , Pessen , H. and McDonald , G. G. 1987 . The formation of intermediate lactones during aminolysis of diethyl xylarate . J. Carbohydr. Chem. , 6 : 495 – 499 .
   Web of Science ®Google Scholar
• Hashimoto , K. , Wibullucksanakul , S. , Matsuura , M. and Okada , M. 1993 . Macromolecular synthesis from saccharic lactones. Ring-opening polyaddition of d-glucaro- and d-mannaro-1,4:6,3-dilactones with alkylenediamines . J. Polym. Sci. Part A: Polym. Chem. , 31 : 3141 – 3149 .
   Web of Science ®Google Scholar
• Kiely , D. E. , Chen , L. and Lin , T-H. 1994 . Hydroxylated nylons based on unprotected esterifed d-glucaric acid by condensation reactions . J. Am. Chem. Soc. , 116 : 571 – 578 .
   Web of Science ®Google Scholar
• Kiely , D. E. , Chen , L. and Lin , T-H. 2000 . Synthetic polyhydroxypolyamides from galactaric, xylaric, d-glucaric and d-mannaric acids and alkylenediamine monomers—some comparisons . J. Polym. Sci. Part A: Polym. Chem. , 38 : 594 – 603 .
   Web of Science ®Google Scholar
• Henkensmeier , D. , Abele , B. C. , Candussio , A. and Thiem , J. 2004 . Synthesis, characterization and degradability of polyamides derived from aldaric acids and chain end functionalized polydimethylsiloxanes . Polymer , 45 : 7053 – 7059 .
   Web of Science ®Google Scholar
• Jahns , T. and Kiely , D. E. 2006 . Abiotic hydrolysis of some poly-d-glucaramides and subsequent microbial utilization / degradation . J. Polym. Environ. , 14 : 165 – 169 .
   Web of Science ®Google Scholar
• Kiely , D. E. 1995 . Carbohydrate acid amide plant fertilizers . 1996 : 56392 U.S. Patent 5,478,374, December 26, CA
   Google Scholar
• Styron , S. B. , French , A. D. , Friedrich , J. D. , Lake , C. and Kiely , D. E. 2002 . MM3(96) Conformational analysis of d-glucaramide and x-ray crystal structures of three d-glucaric acid derivatives - models for synthetic poly(alkylene d-glucaramides) . J. Carbohydr. Chem. , 21 : 27 – 51 .
   Web of Science ®Google Scholar
• Denton , T. T. , Hardcastle , K. I. , Dowd , M. K. and Kiely , D. E. 2011 . Characterization of d-glucaric acid using NMR, x-ray crystal structure and MM3 molecular modeling analyses . Carbohydr. Res. , 346 : 2551 – 2557 .
   PubMed Web of Science ®Google Scholar
• Navarro , E. , Aleman , C. and Puiggali , J. 1995 . Folding of methylene groups in linear glutaraide analogs . J. Am. Chem. Soc. , 117 ( 28 ) : 7307 – 10 . 11 and references therein
   Web of Science ®Google Scholar
• Angyal , S. , LeFur , R. and Gagnaire , D. 1972 . Conformations of acyclic sugar derivatives Part II: determination of the conformations of alditol acetates in solution by the use of 250-MHz NMR spectra . Carbohydr. Res. , 23 : 121 – 134 .
   Web of Science ®Google Scholar
• Sweeting , L. , Coxon , B. and Varma , R. 1979 . Conformational analysis of peracetylated hexononitriles . Carbohydr. Res. , 72 : 43 – 55 .
   Web of Science ®Google Scholar
• Blanc-Muesser , M. , Defaye , J. and Horton , D. 1980 . Conformations in solution of the stereoisomeric, peracetylated aldohexose dimethyl acetals and diethyl dithioacetals . Carbohydr. Res. , 87 : 71 – 86 .
   Web of Science ®Google Scholar
• Zhang , J. , Kiely , D. E. and Hardcastle , K. 2006 . MM3 conformational analysis and X-ray crystal structure of 2,3,4,5-tetra-O-acetyl-N,N′-dimethyl-d-glucaramide as a conformational model for the d-glucaryl unit of poly(alkylene 2,3,4,5-tetra-O-acetyl-d-glucaramides) . J. Carbohydr. Chem. , 25 : 633 – 659 .
   Web of Science ®Google Scholar
• Etter , M. C. 1990 . Encoding and decoding hydrogen-bond patterns of organic compounds . Acc. Chem. Res. , 23 : 120 – 126 .
   Web of Science ®Google Scholar
• Dellinger , J. A. , George , G. D. and Roberts , C. W. 1978 . Synthesis and luminescence properties of model compounds of nylon 6,6. II. α,ω-alkanediamides . J. Polym. Sci., Polym. Lett. Ed. , 16 : 357 – 365 .
   Web of Science ®Google Scholar
• Kaupp , G. , Schmeyers , J. and Boy , J. 2000 . Quantitative solid-state reactions of amines and carbonyl compounds and isothiocyanates . Tetrahedron , 56 : 6899 – 6911 .
   Web of Science ®Google Scholar
• Hinton , M. R. , Manley-Harris , M. , Hardcastle , K. I. and Kiely , D. E. 2013 . Nitric acid oxidation of d-xylose, d-arabinose, l-arabinose, and d-ribose to xylaric, d-arabinaric (d-lyxaric), l-arabinaric (l-lyxaric), and ribaric acids, preceding paper . J. Carbohydr. Chem. , 32 ( 1 ) : 68 – 85 .
   Web of Science ®Google Scholar
• SMART Version 5.55 . 2000 . Analytical X-ray Systems , Madison : Bruker AXS, Inc. . WI 53711–5373
   Google Scholar
• SAINT Version 6.02 . 1999 . Analytical X-ray Systems , Madison : Bruker AXS, Inc. . WI 53711–5373
   Google Scholar
• Sheldrick , G. M. 1997 . SHELX97 Programs for the solution and refinement of crystal structures , 112 – 122 . Germany : University of Göttingen . Sheldrick, G.M. A short history of SHELX. Acta Cryst. 2008, A64
   Google Scholar
• Farrugia , L. J. 1999 . WinGx v 1.70.01 , Edited by: Farrugia , L. J. Vol. 32 , 837 – 838 . UK : University of Glasgow . Win GX suite for small-molecule single-crystal crystallography. J. Appl. Cryst
   Google Scholar
• Farrugia , L. J. 1997 . ORTEP-3 for windows - a version of ORTEP-III with a graphical user interface (GUI) . J. Appl. Cryst. , 30 : 565
   Web of Science ®Google Scholar
• Macrae , C. F. , Bruno , I. J. , Chisholm , J. A. , Edgington , P. R. , McCabe , P. , Pidcock , E. , Rodriguez-Monge , L. , Taylor , R. , van de Streek , J. and Wood , P. A. 2008 . Mercury CSD2.0–new features for the visualization and investigation of crystal structures. J. Appl. Cryst. , 41 : 466 – 470 . Mercury CSD 2.0 - Program for the Visualization and Investigation of Crystal Structures
   Google Scholar