A DFT study of the formation of xanthydrol motifs during electrophilic poly(aryl ether ketone) synthesis

Journal of Molecular Modeling

Volumn 22, Issue 1, 2016, Pages 1-14

  Melissen, Sigismund T A G ^a,b,c   Tognetti, Vincent ^a   Dupas, Georges ^a   Jouanneau, Julien ^b   Lê, Guillaume ^b   Joubert, Laurent ^a  

^a UNIVERSITÉ DE ROUEN   (France)

^b ARKEMA   (France)

^c Laboratoire de Chimie Organique   (France)

Author keywords

Chain termination; Density functional theory; Electrophilic aromatic substitution; Friedel Crafts reactions; Poly(aryl ether ketones); Polymer defect; Stacking; Xanthydrol; B97X D

Indexed keywords

9 PHENYL 9H XANTHEN 9 OL; AROMATIC COMPOUND; BENZOPHENONE DERIVATIVE; CARBONYL DERIVATIVE; ETHER DERIVATIVE; FUNCTIONAL GROUP; KETONE DERIVATIVE; OXYGEN; POLY(ARYL ETHER KETONE); POLYMER; UNCLASSIFIED DRUG; XANTHYDROL;

ACYLATION; ARTICLE; CATALYSIS; CYCLIZATION; DENSITY FUNCTIONAL THEORY; ELECTROPHILICITY; FRIEDEL CRAFTS REACTION; MATHEMATICAL COMPUTING; NUCLEOPHILICITY; PRIORITY JOURNAL; PROTON TRANSPORT; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 84951176064     PISSN: 16102940     EISSN: 09485023     Source Type: Journal    
DOI: 10.1007/s00894-015-2861-4     Document Type: Article

References (78)

1. Salamone JC (1999) Concise polymeric materials encyclopedia, vol 1. CRC Press, Boca Raton
2. Rosato DV, Rosato DV, Rosato MV (2004) Plastic product material and process selection handbook. Elsevier Ltd., Oxford (UK)
3. Johnson RN, Farnham AG, Clendinning RA, Hale WF, Merriam CN (1967) Poly(aryl ethers) by nucleophilic aromatic substitution. I. Synthesis and properties. J Polym Sci Polym Chem 5:2375–2398
4. Attwood TE, Dawson PC, Freeman JL, Hoy LRJ, Rose JB, Staniland PA (1981) Synthesis and properties of polyaryletherketones. Polymer 22:1096–1103
5. Rose JB, Staniland PA (1982) Thermoplastic aromatic polyetherketones. US Patent 4,320,224
6. Fukawa I, Tanabe T, Dozono T (1991) Preparation of aromatic poly(ether ketones) from an aromatic dihalide and sodium carbonate. Macromolecules 24(13):3838–3844
7. Bonner WH (1962) Aromatic polyketones and preparation thereof
8. Goodman I, McIntyre JE, Russell W (1964) British patent 971 227. Chem Abstr 61:14805b
9. Brugel EG (1991) Stabilization of poly(ether ketone ketones). US Patent 4,816,556
10. Gay FP, Brunette CM (1989) Ordered polyketones
11. Rueda DR, Zolotukhin MG, Cagiao ME, Ania F, Dosière M, Villers D, de Abajo J (2001) On the effect of reaction conditions on morphology of aromatic poly(ether-ketone)s, PEKK. J Macromol Sci B 40:709–731
12. Ueda M, Sato M (1987) Macromolecules 20:2675–2678
13. Zolotukhin MG, Rueda DR, Balta Calleja FJ, Cagiao ME, Bruix M, Sedova EA, Gileva NG (1997) Aromatic polymers obtained by precipitation polycondensation: 4. Synthesis of poly(ether ketone ketone)s. Polymer 38:1471–1476
14. Braun D, Cherdron H, Rehahn M, Ritter H, Voit B (2005) Polymer synthesis: theory and practice—fundamentals, methods, experiments. Springer, Berlin (D)
15. Friedel C, Crafts JM (1877) Sur une nouvelle méthode générale de synthèse d’hydrocarbures, d’acétones, etc. Bull Soc Chim Fr 84:1450–1454
16. Olah GA (1963) Friedel–Crafts and related reactions, volume 1, general aspects. Friedel–Crafts and Related Reactions. Wiley Interscience, New York
17. Olah GA (1964) Friedel–Crafts and related reactions, volume 3, acylation and related reactions. Friedel–Crafts and related reactions. Wiley Interscience, New York
18. Eyley SC (1991) 3.1 - The aliphatic Friedel–Crafts reaction. In: Trost BM, Fleming I (eds) Comp Org Synth, vol 2. Pergamon, Oxford, pp 707–731
19. Heaney H (1991) 3.2 - The bimolecular aromatic Friedel–Crafts reaction. Comp Org Synth 2:733–752
20. Heaney H (1991) 3.3 - The intramolecular aromatic Friedel–Crafts reaction. Comp Org Synth 2:753–768
21. Mullins MJ, Woo EP (1987) The synthesis and properties of poly(aromatic ketones). J Macromol Sci Part C 27:313–341
22. Jonas A, Legras R, Devaux J (1992) PEEK oligomers: a model for the polymer physical behavior. 1. Synthesis and characterization of linear monodisperse oligomers. Macromolecules 25:5841–5850
23. Angelo RJ, Darms R, Wysong RD (1973) Melt stable polyketone compositions. Melt Stable Polyketone Compositions. US Patent 3,767,620
24. 6-catalyzed Friedel–Crafts acylation of phenyl aromatic compounds. J Mol Model 19:4947–4958
25. Olah GA, Klumpp DA (2004) Superelectrophilic solvation. Acc Chem Res 37:211–220
26. Olah GA, Germain A, Lin HC, Forsyth DA (1975) Electrophilic reactions at single bonds. XVIII. Indication of protosolvated de facto substituting agents in the reactions of alkanes with acetylium and nitronium ions in superacidic media. J Am Chem Soc 97:2928–2929
27. Defined as acids that are stronger than pure sulphuric acid
28. Cheon CH, Yamamoto H (2011) Super Brönsted acid catalysis. Chem Commun 47:3043–3056
29. Castillo UJ, Zolotukhin MG, Fomina L, Nieto DR, Garza LO, Fomine S (2013) Reactions of ketones with aromatics in acid media. The effect of trifluoromethyl groups and the acidity media. A theoretical study. J Mol Model 19:793–801
30. Peña ER, Zolotukhin M, Fomine S (2004) Factors enhancing the reactivity of carbonyl compounds for polycondensations with aromatic hydrocarbons. A computational study. Macromolecules 37:6227–6235
31. Colquhoun HM, Zolotukhin MG, Khalilov LM, Dzhemilev UM (2001) Superelectrophiles in aromatic polymer chemistry. Macromolecules 34:1122–1124
32. Saito S, Sato Y, Ohwada T, Shudo K (1994) Friedel–Crafts-type cyclodehydration of 1,3-diphenyl-1-propanones. Kinetic evidence for the involvement of dication. J Am Chem Soc 116:2312– 2317
33. Olah GA, Wang Q, Neyer G (1994) Superelectrophilic Methylthiomethylation of Aromatics with Chloromethyl Methyl Sulfide. Synthesis, p. 276
34. Tognetti V, Morell C, Ayers PW, Joubert L, Chermette H (2013) A proposal for an extended dual descriptor: a possible solution when frontier molecular orbital theory fails. Phys Chem Chem Phys 15:14465–14475
35. Guégan F, Mignon P, Tognetti V, Joubert L, Morell C (2014) Dual descriptor and molecular electrostatic potential: complementary tools for the study of the coordination chemistry of ambiphilic ligands. Phys Chem Chem Phys 16:15558–15569
36. Tognetti V, Morell C, Joubert L (2015) Quantifying electro/nucleophilicity by partitioning the dual descriptor. J Comput Chem 36:649–659
37. Derouane D, Harvey JN, Viehe HG (1995) Ring expansion or spirocyclisation of (phenylthiomethylene)cycloalkanes with aluminium chloride via β-thio carbocations. J Chem Soc Chem Commun, pp. 993–994
38. Frisch MJEA, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA (2009) Gaussian 09, Revision B. 01. Gaussian, Inc., Wallingford (CT, USA)
39. Chai J-D, Head-Gordon M (2008) Long-range corrected hybrid density functionals with damped atom–atom dispersion corrections. Phys Chem Chem Phys 10:6615
40. Chai J-D, Head-Gordon M (2008) Systematic optimization of long-range corrected hybrid density functionals. J Chem Phys 128:084106
41. Goerigk L, Grimme S (2011) A thorough benchmark of density functional methods for general main group thermochemistry, kinetics, and noncovalent interactions. Phys Chem Chem Phys 13:6670–6688
42. Chéron N, Jacquemin D, Fleurat-Lessard P (2012) A qualitative failure of B3LYP for textbook organic reactions. Phys Chem Chem Phys 14:7170–7175
43. Zhang IY, Wu J, Xu X (2010) Extending the reliability and applicability of B3LYP. Chem Commun 46:3057–3070
44. Tomasi J, Mennucci B, Cammi R (2005) Quantum mechanical continuum solvation models. Chem Rev 105:2999–3093
45. Miertuš S, Scrocco E, Tomasi J (1981) Electrostatic interaction of a solute with a continuum. A direct utilization of ab initio molecular potentials for the prevision of solvent effects. Chem Phys 55(1):117–129
46. Cancès E, Mennucci B, Tomasi J (1997) A new integral equation formalism for the polarizable continuum model: theoretical background and applications to isotropic and anisotropic dielectrics. J Chem Phys 107(8):3032
47. Li X, Frisch MJ (2006) Energy-represented direct inversion in the iterative subspace within a hybrid geometry optimization method. J Chem Theory Comput 2:835–839
48. Peng CY, Ayala PY, Bernhard Schlegel H, Frisch MJ (1996) Using redundant internal coordinates to optimize equilibrium geometries and transition states. J Comput Chem 17:49–56
49. Fukui K (1981) The path of chemical reactions - the IRC approach. Acc Chem Res 14:363–368
50. Gonzalez C, Bernhard Schlegel H (1989) An improved algorithm for reaction path following. J Chem Phys 90:2154
51. Braga AAC, Ujaque G, Maseras F (2006) A DFT study of the full catalytic cycle of the Suzuki–Miyaura cross-coupling on a model system. Organometallics 25:3647–3658
52. Zielinski F, Tognetti V, Joubert L (2012) Condensed descriptors for reactivity: a methodological study. Chem Phys Lett 527:67–72
53. Xu T, Barich DH, Torres PD, Nicholas JB, Haw JF (1997) Carbon-13 chemical shift tensors for acylium ions: a combined solid state NMR and ab initio molecular orbital study. J Am Chem Soc 119:396–405
54. Cassimatis D, Bonnin JP, Theophanides T (1970) Donor-acceptor interactions in Friedel–Crafts systems. Can J Chem 48:3860–3871
55. 3. J Chem Soc, Dalton Trans, p. 680–685
56. Olah GA (1971) Aromatic substitution. XXVIII. Mechanism of electrophilic aromatic substitutions. Acc Chem Res 4:240–248
57. Olah GA, Kobayashi S, Tashiro M (1972) Aromatic substitution. XXX. Friedel–Crafts benzylation of benzene and toluene with benzyl and substituted benzyl halides. J Am Chem Soc 94:7448–7461
58. Peter Boer F (1968) Crystal structure of a Friedel–Crafts intermediate. Methyloxocarbonium hexafluoroantimonate. J Am Chem Soc 90:6706–6710
59. Chevrier B, Carpentier JML, Weiss R (1972) Synthesis of two crystalline species of the Friedel–Crafts intermediate antimony pentachloride-p-toluoyl chloride. Crystal structures of the donor–acceptor complex and of the ionic salt. J Am Chem Soc 94:5718–5723
60. Yamabe S, Yamazaki S (2009) A remarkable difference in the deprotonation steps of the Friedel–Crafts acylation and alkylation reactions. J Phys Org Chem 22:1094–1103
61. 3 (X = H, F, Cl) interactions. J Phys Chem A 103(45):9116–9124
62. 6 in the catalyzed decomposition of organic halides. J Phys Chem 99(17):6502–6508
63. Volkov AN, Timoshkin AY, Suvorov AV (2005) Pathways of electrophilic aromatic substitution reactions catalyzed by group 13 trihalides: an ab initio study. Int J Quantum Chem 104:256–260
64. Volkov AN, Timoshkin AY, Suvorov AV (2004) On the importance of dimeric forms of Al and Ga trichlorides in the electrophilic aromatic substitution reactions: an ab initio study. Int J Quantum Chem 100:412–418
65. Chattaraj PK, Sarkar U, Elango M, Parthasarathi R, Subramanian V (2005) Electrophilicity as a Possible Descriptor of the Kinetic Behaviour. arXiv:Physics/0509089v [Physics-Chem Phys]
66. Osamura Y, Terada K, Kobayashi Y, Okazaki R, Ishiyama Y (1999) A molecular orbital study of the mechanism of chlorination reaction of benzene catalyzed by Lewis acid. J Mol Struct (THEOCHEM) 461–462:399–416
67. Gothelf AS, Hansen T, Jorgensen KA (2001) Studies on aluminium mediated asymmetric Friedel–Crafts hydroxyalkylation reactions of pyridinecarbaldehydes. J Chem Soc, Perkin Trans 1:854–860
68. 6/Al system. J Am Chem Soc 124:11379–11391
69. Riley KE, Pitoňák M, Jurečka P, Hobza P (2010) Stabilization and structure calculations for noncovalent interactions in extended molecular systems based on wave function and density functional theories. Chem Rev 110:5023–5063
70. Pitoňák M, Neogrády P, Rezáč J, Jurečka P, Urban M, Hobza P, Dimer B (2008) High-level wave function and density functional theory calculations. J Chem Theory Comput 4:1829–1834
71. Kim KS, Karthikeyan S, Jiten Singh N (2011) How different are aromatic π interactions from aliphatic π interactions and non- π stacking interactions J Chem Theory Comput 7:3471–3477
72. Sinnokrot MO, David Sherrill C (2006) High-accuracy quantum mechanical studies of π−π interactions in benzene dimers. J Phys Chem A 110:10656–10668
73. Wheeler SE, Houk KN (2008) Substituent effects in the benzene dimer are due to direct interactions of the substituents with the unsubstituted benzene. J Am Chem Soc 130:10854–10855
74. Bloom JWG, Wheeler SE (2011) Taking the aromaticity out of aromatic interactions. Angew Chemie Int Ed 50:7847–7849
75. Kozuch S, Shaik S (2011) How to conceptualize catalytic cycles? The energetic span model. Acc Chem Res 44:101– 110
76. 1−3 application of the energetic span model
77. Jiang Y-Y, Yu H-Z, Fu Y (2013) Mechanistic study of borylation of nitriles catalyzed by Rh-B and Ir-B complexes via C-CN bond activation. Organometallics 32:926–936
78. Anslyn EV, Dougherty DA (2006) Modern Physical Organic Chemistry. University Science, Sausalito (CA, USA)