Theoretical investigation on the improper hydrogen bond in κ-carrabiose⋯Y (Y = HF, HCl, HBr, NH

Huggins ML (1922) Atomic structure. Science 55:459–460

pubmed: 17809302 doi: 10.1126/science.55.1426.459 pmcid: 17809302

Pauling LJ (1931) The nature of the chemical bond. Application of results obtained from the quantum mechanics and from a theory of paramagnetic susceptibility to the structures of molecules. Am Chem Soc 53:1367–1400

doi: 10.1021/ja01355a027

Scheiner S (1997) Hydrogen bonding. Oxford University Press, New York

Jeffrey GA (1997) An introduction to hydrogen bond. Oxford University Press, New York

Desiraju G, Steiner T (1999) The weak hydrogen bond. Oxford University Press, New York

Kollman PA, Allen LC (1972) Theory of the hydrogen bond. Chem Rev 72:283–303

doi: 10.1021/cr60277a004

Gordon MS, Jensen JH (1996) Understanding the hydrogen bond using quantum chemistry. Acc Chem Res 29:536–543

doi: 10.1021/ar9600594

Morokuma K (1977) Why do molecules interact? The origin of electron-donor acceptor complexes, hydrogen bonding and proton affinity. Acc Chem Res 10:294–300

doi: 10.1021/ar50116a004

Liu S, Dykstra CEJ (1986) A theory of vibrational transition frequency shifts due to hydrogen bonding. Phys Chem 90(14):3097–3103

doi: 10.1021/j100405a013

Bader RFW (1964) A model for the hydrogen bond and proton transfer reactions. Can J Chem 42:1822–1834

doi: 10.1139/v64-274

Ratajczak HJ (1972) Charge-transfer properties of the hydrogen bond. I. Theory of the enhancement of dipole moment of hydrogen-bonded systems. Phys Chem 76:3000–3004

doi: 10.1021/j100665a013

Allerhand A, Schleyer PvR (1963) A survey of C-H groups as proton donors in hydrogen bonding. J Am Chem Soc 85:1715–1723

doi: 10.1021/ja00895a002

Sandorfy C (1984) Vibrational spectra of hydrogen bonded systems in the gas phase. Top Curr Chem 120:41–84

doi: 10.1007/3-540-12785-2_2

Zierkiewicz W, Jurečka P, Hobza P (2005) On differences between hydrogen bonding and improper blue-shifting hydrogen bonding. ChemPhysChem 6:609–617

pubmed: 15881576 doi: 10.1002/cphc.200400243 pmcid: 15881576

Badger RM, Bauer SH (1937) Spectroscopic studies of the hydrogen bond. II. The shift of the O-H vibrational frequency in the formation of the hydrogen bond. J Chem Phys 5:839

doi: 10.1063/1.1749952

Nakamoto K, Margolis M, Rundel RE (1955) Stretching frequencies as a function of distances in hydrogen bonds. J Am Chem Soc 77:6480–6486

doi: 10.1021/ja01629a013

Ojamae L, Hermansson K (1992) Water molecules in different crystal surroundings: Vibrational O-H frequencies from ab initio calculations. J Chem Phys 96:9035–9044

doi: 10.1063/1.462262

Szczepaniak K, Tramer A (1967) Charge-transfer model and infrared spectra of hydrogen-bonded complexes of .pi.-electron donors. J Phys Chem 71:3035–3039

doi: 10.1021/j100868a040

Pinchas S (1957) Infrared absorption of aldehydic C-H group. Anal Chem 29:334–339

doi: 10.1021/ac60123a003

Pinchas S (1963) Intramolecular hydrogen bonding in O-nitrobenzaldehyde and related compounds. J Phys Chem 67:1862–1865

doi: 10.1021/j100803a030

Satonaka H, Abe K, Hirota M (1987)

doi: 10.1246/bcsj.60.953

Budesinsky M, Fiedler P, Arnold Z (1989) Triformylmethane: an efficient preparation, some derivatives, and spectra. Synthesis 11:858–860

doi: 10.1055/s-1989-27411

Boldeskul IE, Tsymbal IF, Ryltsev EV, Latajka Z, Barnes AJ (1997) Reversal of the usual ν HD spectral shift of haloforms in some hydrogen-bonded complexes. J Mol Struct 37:167–171

doi: 10.1016/S0022-2860(97)00137-3

Caminati W, Melandri S, Moreschini P, Favero PG (1999) The C-F small middle dot small middle dot small middle dotH-C “anti-hydrogen bond” in the gas phase: microwave structure of the difluoromethane dimer. Angew Chem Int Ed 38:2924–2925

doi: 10.1002/(SICI)1521-3773(19991004)38:19<2924::AID-ANIE2924>3.0.CO;2-N

Mizuno K, Imafuji S, Ochi T, Ohta T, Maeda SJ (2000) Hydration of the CH groups in dimethyl sulfoxide probed by NMR and IR. Phys Chem B 104:11001–11005

doi: 10.1021/jp001079x

Goutev N, Matsuura H (2001) Hydrogen bonding in chloroform solutions of ethylenedioxy ethers. Spectroscopic Evidence of Bifurcated Hydrogen Bonds. J Phys Chem A 105:4741–4748

doi: 10.1021/jp004542e

Reimann B, Buchhold K, Vaupel S, Brutschy BZ (2001) Blue-shift in the frequencies of the CH stretches of chloro- and fluoroform induced by C-H...π hydrogen bonding with benzene derivatives: the influence of electron donating and withdrawing substituents. Phys Chem 215:777–793

Afonin AV, Andriyankov MA (1988) Zh Org Khim 24:1034

Cubero E, Orozco M, Hobza P, Luque FJ (1999) Hydrogen bond versus anti-hydrogen bond: a comparative analysis based on the electron density topology. J Phys Chem A 103:6394–6401

doi: 10.1021/jp990258f

van der Veken BJ, Herrebout WA, Szostak R, Shchepkin DN, Havlas Z, Hobza P (2001) The nature of improper, blue-shifting hydrogen bonding verified experimentally. J Am Chem Soc 123:12290–12293

pubmed: 11734029 doi: 10.1021/ja010915t pmcid: 11734029

Hobza P, Havlas Z (2000) Blue-shifting hydrogen bonds. Chem Rev 100:4253–4264

pubmed: 11749346 doi: 10.1021/cr990050q pmcid: 11749346

Zierkiewicz W, Czarnik-Matusewicz B, Michalska D (2011) Blue shifts and unusual intensity changes in the infrared spectra of the enflurane···acetone complexes: spectroscopic and theoretical studies. J Phys Chem A 115:11362–11368

pubmed: 21913646 doi: 10.1021/jp205081r pmcid: 21913646

Zierkiewicz W, Zalesny R, Hobza P (2013) On the nature of unusual intensity changes in the infrared spectra of the enflurane⋯acetone complexes. Phys Chem Chem Phys 15:6001–6007

pubmed: 23493886 doi: 10.1039/c3cp50385b pmcid: 23493886

Trudeau GT, Dumas JM, Dupuis P, Guerin M, Sandorfy C (1980) Intermolecular interactions and anesthesia: infrared spectroscopic studies. Top Curr Chem 93:91–125

pubmed: 7008260 doi: 10.1007/3-540-10058-X_9 pmcid: 7008260

Nishio M, Hirota M, Umezawa Y (1998) The CH/π interaction. Evidence Nature and Consequences. Wiley-VCH, New York

Hobza P, Špirko V, Selzle HL, Schlag EW (1998) Anti-hydrogen bond in the benzene dimer and other carbon proton donor complexes. J Phys Chem A 102:2501–2504

doi: 10.1021/jp973374w

Hobza P, Špirko V, Havlas Z, Buchhold K, Reimann B, Barth HD, Brutschy B (1999) Anti-hydrogen bond between chloroform and fluorobenzene. Chem Phys Lett 299:180–186

doi: 10.1016/S0009-2614(98)01264-0

Reimann B, Buchhold K, Vaupel S, Brutschy B, Havlas Z, Špirko V, Hobza P (2001) Improper, blue-shifting hydrogen bond between fluorobenzene and fluoroform. J Phys Chem A 105:5560–5566

doi: 10.1021/jp003726q

Solimannejad M, Gharabaghi M, Scheiner S (2011) SH···N and SH···P blue-shifting H-bonds and N···P interactions in complexes pairing HSN with amines and phosphines. J Chem Phys 134:024312 ((1-6))

pubmed: 21241104 doi: 10.1063/1.3523580 pmcid: 21241104

Tuttle T, Graefenstein J, Wu A, Kraka E, Cremer D (2004) Analysis of the NMR spin−spin coupling mechanism across a H−bond: nature of the H-bond in proteins. J Phys Chem B 108:1115–1129

doi: 10.1021/jp0363951

Brauer B, Gerber RB, Kabelac M, Hobza P, Bakker JM, Riziq AGA, de Vries MS (2005) Vibrational spectroscopy of the G...C base pair: experiment, harmonic and anharmonic calculations, and the nature of the anharmonic couplings. J Phys Chem A 109:6974–6974

pubmed: 16834057 doi: 10.1021/jp051767m pmcid: 16834057

Li XS, Liu L, Schlegel HB (2002) On the physical origin of blue-shifted hydrogen bonds. J Am Chem Soc 124:9639–9647

pubmed: 12167060 doi: 10.1021/ja020213j pmcid: 12167060

Fan JM, Liu L, Guo QX (2002) Substituent effects on the blue-shifted hydrogen bonds. Chem Phys Lett 365:464–472

doi: 10.1016/S0009-2614(02)01487-2

McDowell SAC, Buckingham AD (2005) On the correlation between bond-length change and vibrational frequency shift in hydrogen-bonded complexes: a computational study of Y···HCl dimers (Y = N

pubmed: 16262415 doi: 10.1021/ja0543651 pmcid: 16262415

Szostak R (2011) Blue or red Δν

doi: 10.1016/j.cplett.2011.09.082

Raghavendra B, Arunan E (2007) Unpaired and σ bond electrons as H, Cl, and Li bond acceptors: an anomalous one-electron blue-shifting chlorine bond. J Phys Chem A 111:9699–9706

pubmed: 17760431 doi: 10.1021/jp073667h pmcid: 17760431

Alabugin IV, Manoharan M, Weinhold FA (2004) Blue-shifted and red-shifted hydrogen bonds in hypervalent rare-gas FRg−H···Y sandwiches. J Phys Chem A 108:4720–4730

doi: 10.1021/jp049723l

Lignell A, Khriachtchev L, Pettersson M, Räsänen M (2002) Large blueshift of the H-Kr stretching frequency of HKrCl upon complexation with N2. J Chem Phys 117:961–964

doi: 10.1063/1.1491403

McDowell SAC (2003) Blue-shifting hydrogen bonding in N2⋯HKrF. J Chem Phys 118:7283–7287

doi: 10.1063/1.1564059

Hobza P, Havlas Z (1999) The fluoroform⋯ethylene oxide complex exhibits a C-H⋯O anti-hydrogen bond. Chem Phys Lett 303:447–452

doi: 10.1016/S0009-2614(99)00217-1

Zierkiewicz W, Michalska D, Havlas Z, Hobza P (2002) Study of the nature of improper blue-shifting hydrogen bonding and standard hydrogen bonding in the X

pubmed: 12465490 doi: 10.1002/1439-7641(20020617)3:6<511::AID-CPHC511>3.0.CO;2-Y pmcid: 12465490

Gu Y, Kar T, Scheiner S (1999) Fundamental properties of the CH···O interaction: is it a true hydrogen bond? J Am Chem Soc 121:9411–9422

doi: 10.1021/ja991795g

Scheiner S, Kar T, Gu Y (2001) Strength of the C

pubmed: 11152477 doi: 10.1074/jbc.M010770200 pmcid: 11152477

Dykstra CE (1988) Intermolecular electrical interaction: a key ingredient in hydrogen bonding. Acc Chem Res 21:355–361

doi: 10.1021/ar00154a001

Qian WL, Krimm S (2005) Limitations of the molecular multipole expansion treatment of electrostatic interactions for C−H···O and O−H···O hydrogen bonds and application of a general charge density approach. J Phys Chem A 109:5608–5618

pubmed: 16833893 doi: 10.1021/jp040683v pmcid: 16833893

Bent H (1961) An appraisal of valence-bond structures and hybridization in compounds of the first-row elements. Chem Rev 61:275–311

doi: 10.1021/cr60211a005

Alabugin IV, Manoharan M, Peabody S, Weinhold F (2003) Electronic basis of improper hydrogen bonding: a subtle balance of hyperconjugation and rehybridization. J Am Chem Soc 125:5973–5987

pubmed: 12733938 doi: 10.1021/ja034656e pmcid: 12733938

Reed AE, Curtiss LA, Weinhold F (1988) Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint. Chem Rev 88:899–926

doi: 10.1021/cr00088a005

Joseph J, Jemmis ED (2007) Red-, Blue-, or No-shift in hydrogen bonds: a unified explanation. J Am Chem Soc 129:4620–4532

pubmed: 17375920 doi: 10.1021/ja067545z pmcid: 17375920

Grabowski SJ (2011) Red- and blue-shifted hydrogen bonds: the bent rule from quantum theory of atoms in molecules perspective. J Phys Chem A 115:12789–12799

pubmed: 21830803 doi: 10.1021/jp203908n pmcid: 21830803

Moir A, Smith DA (1990) The genetics of bacterial spore germination. J Annu Rev Microbiol 44:531–553

doi: 10.1146/annurev.mi.44.100190.002531

Lee C, Yang W, Parr RG (1988) Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B 37:785–789

doi: 10.1103/PhysRevB.37.785

Adamo C, Barone V (1999) Toward reliable density functional methods without adjustable parameters: the PBE0 model. J Chem Phys 110:6158–6169

doi: 10.1063/1.478522

Ernzerhof M, Scuseria GE (1999) Assessment of the Perdew–Burke–Ernzerhof exchange-correlation functional. J Chem Phys 110:5029–5036

doi: 10.1063/1.478401

Zhao Y, Truhlar DG (2008) The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functional. Theor Chem Acc 120:215–241

doi: 10.1007/s00214-007-0310-x

Afonin AV, Vashchenko AV (2010) DFT prediction of anomalously large blue shift of the C-H stretching frequency in 2-vinyloxypyridine and -quinoline due to the intramolecular C–H···N hydrogen bonding. J Mol Struct (THEOCHEM) 940:56–60

doi: 10.1016/j.theochem.2009.10.004

Chandra AK, Parveen S, Das S, Zeegers-Huyskens T (2008) Blue shifts of the C-H stretching vibrations in hydrogen-bonded and protonated trimethylamine. Effect of hyperconjugation on bond properties. J Comput Chem 29:1490–1496

pubmed: 18270959 doi: 10.1002/jcc.20910 pmcid: 18270959

Xu Z, Li H, Wang C, Wu T, Han S (2004) Is the blue shift of C-H vibration in DMF–water mixture mainly caused by C–H⋯O interaction? Chem Phys Lett 394:405–409

doi: 10.1016/j.cplett.2004.07.051

Zierkiewicz W, Jurecˇka P, Hobza P (2005) On differences between hydrogen bonding and improper blue-shifting hydrogen bonding. Chem Phys Chem 6:609–617

pubmed: 15881576 doi: 10.1002/cphc.200400243 pmcid: 15881576

Fodil R, Sekkal-Rahal M, Sayede A (2017) Testing the CP-correction procedure with different DFT methods on H-bonding complexes of κ-carrabiose with water molecules. J Mol Model 23:31–40

pubmed: 28091888 doi: 10.1007/s00894-016-3199-2 pmcid: 28091888

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. J Chem Theory Comput 2:364–382

pubmed: 26626525 doi: 10.1021/ct0502763 pmcid: 26626525

Ochterski JW, Petersson GA, Montgomery JA (1996) A complete basis set model chemistry. V. Extensions to six or more heavy atoms. J Chem Phys 104:2598–2619

doi: 10.1063/1.470985

Montgomery JAM, Frisch J, Ochterski JW, Petersson GA (2000) A complete basis set model chemistry. VII. Use of the minimum population localization method. J Chem Phys 112:6532–6542

doi: 10.1063/1.481224

Bestaoui-Berrekhchi-Berrahma N, Sekkal-Rahal M, Derreumaux P, Yousfi N (2016) MP2 and DFT studies of β-D-neocarrabiose and β-D-neocarrabiose monohydrate. J Comput Theo Chem 1091:24–30

doi: 10.1016/j.comptc.2016.07.009

Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA Jr, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas Ö, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2009) Gaussian, Inc., Wallingford

Huang Z, Yu W, Lin Z (2006) Exploration of the full conformational landscapes of gaseous aromatic amino acid phenylalanine: an ab initio study. J Mol Struct (THEOCHEM). 758:195–202

doi: 10.1016/j.theochem.2005.10.043

Sekkal M (1990) Utilisation spectrometrie IRTF et de la modélisation moléculaire à l’étude structurale des carraghénanes. Doctoral thesis, Université des sciences et techniques de Lille Flandres Artois

Sekkal M, Legrand P (1993) A spectroscopic investigation of the carrageenans and agar in the 1500–100 cm− 1 spectral range. Spectrochim Acta Part A 49:209–221

doi: 10.1016/0584-8539(93)80176-B

Foster JP, Weinhold F (1980) Natural hybrid orbitals. J Am Chem Soc 102:7211–7218

doi: 10.1021/ja00544a007

Reed AE, Weinhold F (1983) Natural bond orbital analysis of near-Hartree–Fock water dimer. J Chem Phys 78:4066–4073

doi: 10.1063/1.445134

Carpenter JE, Weinhold F (1988) Analysis of the geometry of the hydroxymethyl radical by the “different hybrids for different spins” natural bond orbital procedure. J Mol Struct (THEOCHEM) 46:41–62

doi: 10.1016/0166-1280(88)80248-3

Weinhold F, Carpenter JE (1988) The natural bond orbital Lewis structure concept for molecules, radicals, and radical ions. In: Naaman R, Vager Z (eds) The structure of small molecules and ions. Plenum, New York, pp 227–236

doi: 10.1007/978-1-4684-7424-4_24

Yousfi N, Sekkal-Rahal M, Sayede A, Springborg M (2010) Relaxed energetic maps of kappa-carrabiose: a DFT study. J Comput Chem 31:1312

pubmed: 20127880 pmcid: 20127880

Bekri L, Zouaoui-Rabah M, Springborg M, Sekkal RM (2018) A structural DFT study of MM, GG, MG, and GM alginic acid disaccharides and reactivity of the MG metallic complexes. J Mol Model 24:312–324

pubmed: 30306270 doi: 10.1007/s00894-018-3845-y pmcid: 30306270

Sekkal-Rahal M, Sekkal N, Kleb DC, Bleckmann P (2003) Structures and energies of D-galactose and galabiose conformers as calculated by ab initio and semiempirical methods. J Comput Chem 24:806–818

doi: 10.1002/jcc.10223

Mo Y, Wang C, Guan L, Braïda B, Hiberty PC, Wu W (2014) On the nature of blueshifting hydrogen bonds. Chem Eur J 20:8444–8452

pubmed: 24862363 doi: 10.1002/chem.201402189 pmcid: 24862363

HyperChem® Release 7 for Windows, Hardware lock HyperChem Inc. Florida 32601 USA

Špirko V, Hobza P (2006) Theoretical investigations into the blue-shifting hydrogen bond in benzene complexes. ChemPhysChem 7:640–643

pubmed: 16514693 doi: 10.1002/cphc.200500565 pmcid: 16514693

Kryachko ES, Zeegers-Huyskens T (2002) Theoretical study of the CH···X

doi: 10.1021/jp020426v

Hobza P (2001) The H-index unambiguously discriminates between hydrogen bonding and improper blue-shifting hydrogen bonding. Phys Chem Chem Phys 3:2555–2556

doi: 10.1039/b103068j

Theoretical investigation on the improper hydrogen bond in κ-carrabiose⋯Y (Y = HF, HCl, HBr, NH

Journal

Informations de publication

Résumé

Identifiants

Types de publication

Langues

Sous-ensembles de citation

Pagination

Informations de copyright

Références

Auteurs

Fodil Rachida (F)

Sayede Adlane (S)

Sekkal-Rahal Majda (SR)

Classifications MeSH