Interference of H-bonding and substituent effects in nitro- and hydroxy-substituted salicylaldehydes

Williams JW, Sadle A (1940) The reactions of ketene with salicylaldehyde and p-hydroxybenzaldehyde. J Am Chem Soc 62:2801–2803 Sacconi L, Bertini I (1966) Complexes of copper(II) with Schiff bases formed from salicylaldehydes and N-substituted ethylenediamines. Inorg Chem 5:1520–1522 Sales ZS, Mani NS (2009) An efficient intramolecular 1,3-dipolar cycloaddition involving 2-(1,2-dichlorovinyloxy) aryldiazomethanes: a one-pot synthesis of benzofuropyrazoles from salicylaldehydes. J Org Chem 74:891–894 Zhao H, Neamati N, Sunder S, Hong H, Wang S, Milne GWA, Pommier Y, Burke TR Jr (1997) Hydrazide-containing inhibitors of HIV-1 integrase. J Med Chem 40:937–941 Wang PH, Keck JG, Lien EJ, Lai MMC (1990) Design, synthesis, testing, and quantitative structure–activity relationship analysis of substituted salicylaldehyde schiff bases of 1-amino-3-hydroxyguanidine tosylate as new antiviral agents against coronavirus. J Med Chem 33:608–614 Chinigo GM, Paige M, Grindrod S, Hamel E, Dakshanamurthy S, Chruszcz M, Minor W, Brown ML (2008) Asymmetric synthesis of 2,3-dihydro-2-arylquinazolin-4-ones: methodology and application to a potent fluorescent tubulin inhibitor with anticancer activity. J Med Chem 51:4620–4631 Abd-Elzaher MM, Moustafa SA, Labib AA, Ali MM (2010) Synthesis, characterization, and anticancer properties of ferrocenyl complexes containing a salicylaldehyde moiety. Monatsh Chem 141:387–393 Prisakar VI, Tsapkov VI, Buracheéva SA, Byrké MS, Gulya AP (2005) Synthesis and antimicrobial activity of coordination compounds of copper with substituted salicylaldehyde thiosemicarbazones. Pharm Chem J 39:313–315 Lazzarato L, Donnola M, Rolando B, Marini E, Cena C, Coruzzi G, Guaita E, Morini G, Fruttero R, Gasco A, Biondi S, Ongini E (2008) Searching for new no-donor aspirin-like molecules: a new class of nitrooxy-acyl derivatives of salicylic acid. J Med Chem 51:1894–1903 Gothelf KV, Thomsen A, Nielsen M, Clo E, Brown RS (2004) Modular DNA-programmed assembly of linear and branched conjugated nanostructures. J Am Chem Soc 126:1044–1046 Chung G, Kwon O, Kwon Y (1998) Theoretical study on salicylaldehyde and 2-mercaptobenzaldehyde: intramolecular hydrogen bonding. J Phys Chem A 102:2381–2387 Catalãn J, Torlblo F, Acuña AU (1982) Intramolecular hydrogen bonding and fluorescence of salicylaldehyde, salicylamide, and o-hydroxyacetophenone in gas and condensed phases. J Phys Chem 86:303–306 Schreiber V, Melikova S, Rutkowski K, Shchepkin D, Shurukhina A, Koll A (1996) Temperature dependence studies and model calculations of ν(OH) and ν(OD) band shapes of salicylaldehyde. J Mol Struct 381:141–148 Lampert H, Mikenda W, Karpfen A (1997) Molecular geometries and vibrational spectra of phenol, benzaldehyde, and salicylaldehyde: experimental versus quantum chemical data. J Phys Chem A 101:2254–2263 Filarowski A, Koll A, Sobczyk L (2009) Vibrational spectra of o-hydroxyphenyl Schiff bases and related compounds. Curr Org Chem 13:287–298 Cuma M, Scheiner S, Kar T (1999) Effect of adjoining aromatic ring upon excited state proton transfer, o-hydroxybenzaldehyde. J Mol Struct THEOCHEM 467:37–49 Graña AM, Ríos MA, Rodríguez J (1991) Ab Initio study of the structure and tautomerism of internally hydrogen-bonded aromatic carbonyls: salicylaldehyde and o-hydroxyacetophenone. Struct Chem 2:575–580 Kovács A, Szabó A, Hargittai I (2002) Structural characteristics of intramolecular hydrogen bonding in benzene derivatives. Acc Chem Res 35:887–894 Borisenko KB, Bock CW, Hargittai I (1996) Molecular geometry of benzaldehyde and salicylaldehyde: a gas-phase electron diffraction and ab initio molecular orbital investigation. J Phys Chem 100:7426–7434 Gilli G, Belluci F, Ferretti V, Bertolesi V (1989) Evidence for resonance-assisted hydrogen bonding from crystal-structure correlations on the enol form of the β-diketone fragment. J Am Chem Soc 111:1023–1028 Grabowski SJ (ed) (2006) Hydrogen bonding—new insights. Challenges and advances in computational chemistry and physics 3. Springer, Dordrecht Sobczyk L, Grabowski SJ, Krygowski TM (2005) Interrelation between H-bond and Pi-electron delocalization. Chem Rev 105:3513–3560 Takahashi O, Kohno Y, Nishio M (2010) Relevance of weak hydrogen bonds in the conformation of organic compounds and bioconjugates: evidence from recent experimental data and high-level ab Initio MO calculations. Chem Rev 110:6049–6076 Frey PA, Cleland WW (1998) Are there strong hydrogen bonds in aqueous solutions? Bioorg Chem 26:175–192 Gerlt JA, Kreevoy MM, Cleland WW, Frey PA (1997) Understanding enzymic catalysis: the importance of short, strong hydrogen bonds. Chem Biol 4:259–267 Desiraju GR (1989) Crystal engineering. The design of organic solids. Elsevier, Amsterdam Jeffrey GA, Saenger W (1990) Hydrogen bonding in biological structures. Springer, Berlin Desiraju GR (2002) Hydrogen bridges in crystal engineering: interactions without borders. Acc Chem Res 35:565–573 Gilli G, Gilli P (2009) The nature of the hydrogen bond: outline of the comprehensive hydrogen bond theory. Oxford University Press, Oxford Jezierska A, Panek JJ, Mazzarello R (2009) Structural and electronic structure differences due to the O–H···O and O–H···S bond formation in selected benzamide derivatives: a first-principles molecular dynamics study. Theor Chem Acc 124:319–330 Jezierska A, Novič M, Panek JJ (2009) The nature of hydrogen bonding in selected hydrazide derivatives investigated via static models and Car-Parrinello molecular dynamics. Pol J Chem 83:799–819 Hammett LP (1970) Physical organic chemistry, 2nd edn. McGraw-Hill, New York Exner O (1972) In: Chapman NB, Shorter J (eds) Advances in linear free energy relationships. Plenum, London Johnson CD (1973) The Hammett equation. Cambridge University Press, Cambridge Charton M (1981) Electrical effect substituent constants for correlation analysis. Progr Phys Org Chem 13:119–251 Exner O (1988) In: Chapman NB, Shorter J (eds) Correlation analysis of chemical data. Plenum, New York Shorter J (1991) In: Zalewski RI, Krygowski TM, Shorter J (eds) Similarity models in organic chemistry, biochemistry and related fields. Elsevier, Amsterdam Hansch C, Leo A, Taft RW (1991) A survey of hammett substituent constants and resonance and field parameters. Chem Rev 91:165–195 Exner O, Bohm S (2006) Theory of substitueut effects: recent advances. Curr Org Chem 10:763–778 Krygowski TM, Stępień BT (2005) Sigma- and pi-electron delocalization: focus on substituent effects. Chem Rev 105:3482–3512 Krygowski TM, Szatyłowicz H (2006) Interrelation between the substituent effects, pi-electron delocalization and H-bonding. Trends Org Chem 11:37–53 Krygowski TM, Szatyłowicz H (2008) Modeling the Intermolecular H-bonded systems with varying energy of interactions: substituted phenols. In: Putz MV (ed) Advances in quantum vhemical bonding structures. Transworld Research Network, Kerala, India, pp 287–308 Grabowski SJ (2001) An estimation of strength of intramolecular hydrogen bonds—ab initio and AIM studies. J Mol Struct 562:137–143 Grabowski SJ (2002) Properties of a ring critical point as measures of intramolecular H-bond strength. Monatsh Chem 133:1373–1380 Grabowski SJ (2005) π-Electron delocalisation for intramolecular resonance assisted hydrogen bonds. J Phys Org Chem 16:797–802 Krygowski TM, Zachara JE (2005) How pi-electron delocalisation reflects replacement of H + with Li + in variously substituted malonaldehydes. Theor Chem Acc 114:229–234 Krygowski TM, Zachara-Horeglad JE (2009) Resonance-assisted hydrogen bonding in terms of substituent effect. Tetrahedron 65:2010–2014 Bertolasi V, Gilli P, Ferretti V, Gilli G (1991) Evidence for resonance-assisted hydrogen-bonding.2. Intercorrelation between crystal-structure and spectroscopic parameters in 8 intramolecularly hydrogen-bonded 1,3-diaryl-1,3-propanedione enols. J Am Chem Soc 113:4917–4925 Gilli P, Bertolasi V, Ferretti V, Gilli G (1994) Covalent nature of the strong homonuclear hydrogen-bond-study of the O–H–O system by crystal-structure correlation methods. J Am Chem Soc 116:909–915 Bertolasi V, Gilli P, Ferretti V, Gilli G (1996) Resonance-assisted O-H⋯O hydrogen bonding: Its role in the crystalline self-recognition of beta-diketone enols and its structural and IR characterization. Chem Eur J 2:925–934 Gilli G, Gilli P (2000) Towards an unified hydrogen-bond theory. J Mol Struct 552:1–15 Gilli P, Pretto L, Bertolasi V, Gilli G (2009) Predicting hydrogen-bond strengths from acid-base molecular properties. The pKa slide rule: toward the solution of a long-lasting problem. Acc Chem Res 42:33–44 Krygowski TM, Zachara JE, Szatyłowicz H (2004) Molecular geometry as a source of chemical information. 3. How H-bonding affects aromaticity of the ring in the case of phenol and p-nitrophenol complexes: A B3LYP/6-311 + G** study. J Org Chem 69:7038–7043 Krygowski TM, Szatyłowicz H, Zachara JE (2004) How H-bonding affects aromaticity of the ring in variously substituted phenol complexes with bases. 4. Molecular geometry as a source of chemical information. J Chem Inf Comput Sci 44:2077–2082 Krygowski TM, Szatyłowicz H, Zachara JE (2005) Molecular geometry as a source of chemical information. 5. Substituent effect on proton transfer in para-substituted phenol complexes with fluorides at B3LYP/6-311 + G**. J Chem Inf Model 45:652–656 Szatyłowicz H, Krygowski TM, Zachara-Horeglad JE (2007) Long-distance structural consequences of H-bonding. How H-bonding affects aromaticity of the ring in variously substituted aniline/anilinium/anilide complexes with bases and acids. J Chem Inf Model 47:875–886 Estácio SG, Cabral do Couto P, Costa Cabral BJ, Minas Da Piedade ME, Martinho Simões JA (2004) Energetics of intramolecular hydrogen bonding in di-substituted benzenes by the ortho-para method. J Phys Chem A 108:10834–10843 Scheiner S, Kar T, Čuma M (1997) Excited state intramolecular proton transfer in anionic analogues of malonaldehyde. J Phys Chem A 101:5901–5909 Lipkowski P, Koll A, Karpfen A, Wolschann P (2002) An approach to estimate the energy of the intramolecular hydrogen bond. Chem Phys Lett 360:256–263 Jabłoński M, Kaczmerek A, Sadlej AJ (2006) Estimates of the energy of intramolecular hydrogen bonds. J Phys Chem A 110:10890–10898 Deshmukh MM, Gadre SR, Bartolotti LJ (2006) Estimation of intramolecular hydrogen bond energy via molecular tailoring approach. J Phys Chem A 110:12519–12523 Pross A, Radom L, Taft RW (1980) Theoretical approach to substituent effects—phenols and phenoxide ions. J Org Chem 45:818–826 George P, Trachtmann M, Bock CW, Brett AM (1975) Alternative approach to problem of assessing stabilization energies in cyclic conjugated hydrocarbons. Theor Chim Acta 38:121–129 Krygowski TM, Zachara-Horeglad JE, Palusiak M (2010) H-bonding-assisted substituent effect. J Org Chem 75:4944–4949 Hohenberg P, Kohn W (1964) Inhomogeneous electron gas. Phys Rev 136:B864–B871 Kohn W, Sham LJ (1965) Self-consistent equations including exchange and correlation effects. Phys Rev 140:A1133–A1138 Møller C, Plesset MS (1934) Note on an approximation treatment for many-electron systems. Phys Rev 46:618–622 Krishnan R, Binkley JS, Seeger R, Pople JA (1980) Self-consistent molecular-orbital methods. 20. Basis set for correlated wave-functions. J Chem Phys 72:650–654 Dunning TH Jr (1989) Gaussian-basis sets for use in correlated molecular calculations. 1. The atoms boron through neon and hydrogen. J Chem Phys 90:1007–1023 Becke AD (1993) Density-functional thermochemistry. III. The role of exact exchange. J Chem Phys 98:5648–5652 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 Condens Matter Mater Phys 37:785–789 Dietrich SW, Jorgensen EC, Kollman PA, Rothenberg S (1976) A theoretical study of intramolecular hydrogen bonding in ortho-substituted phenols and thiophenols. J Am Chem Soc 98:8310–8324 Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA (2003) Gaussian03, Rev C02. Gaussian Inc, Wallingford CT 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 NJ, 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 09, Rev A1. Gaussian Inc, Wallingford CT IsisDraw v2.3. © 1990–2000 MDL Information System, Inc