@D_B_McConnell @lauravlaeren "The o/w partitioning system is arbitrary & it has been suggested [17] that its adoption may reflect misinterpretation of work by Collander [25] who was aware of the relevance of the hydrogen bonding characteristics of the
RT @pwk2013: @D_B_McConnell @RenzoCarlucci My preferred way to quantify polarity of compounds is as difference between alkane/water logP fo…
@D_B_McConnell @RenzoCarlucci My preferred way to quantify polarity of compounds is as difference between alkane/water logP for compound and for hypothetical compound with the same molecular surface area. Discussed in HBDs in DD and introduced in: https:/
RT @pwk2013: @KurtzmanTom @D_B_McConnell @KamranHaider501 I'd shifted away from thinking in terms of secondary interactions to frustrated s…
@KurtzmanTom @D_B_McConnell @KamranHaider501 I'd shifted away from thinking in terms of secondary interactions to frustrated solvation when I submitted https://t.co/ThBMTUlkhL in Aug 2016 and had cited less relevant literature. Kamran et al article will b
@D_B_McConnell In LeadOpt HBAs, HBDs and ionizable groups tend to be relatively well conserved and logP:oct may still work well (see “Despite its limitations, logP: oct…” in https://t.co/ThBMTUlkhL ) (4/4)
@ChemBellenie @D_B_McConnell I use the @OpenEyeSoftware spixcoli toolkit which uses the 3D molecular structure (and is therefore conformation dependent). This article may be relevant https://t.co/ThBMTUlkhL
@D_B_McConnell @GastreichM HB donors, HB acceptors and ionizable functional groups tend to be relatively conserved within structural series and so octanol/water logP can often usefully quantify variation in lipophilicity for LeadOpt https://t.co/ThBMTUlkhL
@D_B_McConnell @JasonColeCCDC @ccdc_cambridge I'd certainly use a centroid to define distance (and probably a ring normal to define direction). If interested in calculating MEP minima (Vmin) associated with bonds, there is @OpenEyeSoftware-based code in S
@DennisWhom @QuantumTessera @SuperScienceGrl This article may be relevant to the discussion and it also raises the question as to whether octanol/water is the most appropriate partitioning system for drug discovery DOI https://t.co/ThBMTUlkhL
@Fahima_Chem @MatToddChem @dana_klug @OSantibiotics @DiamondLightSou The last of the supplemental information files (a zip archive) for the following article includes a spreadsheet (in text format) of hydrogen bond basicity measurements with lit refs that
@davidlmobley @jchodera @curiouswavefn @neysanev @openforcefield @JMedChem (3/3) There is a a spreadsheet of measured pKBHX values extracted from the literature in the supplemental material for this article (you'll need to double check the values but there
@TheUnknownChem1 @curiouswavefn @jchodera I'm not sure I know the answer myself and, in any case, I never berate those who genuinely seek the truth. I suspect that some of effect of Cl is to weaken the #HB basicity of π-cloud of aromatic ring. Discussed in
@gtresadern @chem4biology Latest version of software (created using #OEChem from @OpenEyeSoftware) for setting up Gaussian input for calculating HB basicity and pKBHX and logPalk measured data are available in SI of JCAMD 2017 31:163-181 https://t.co/ThBMT
@ChemBioChem @AnneImberty @UNI_FIRENZE Molecular recognition characteristics that could be exploited in design? (1) Hydration of polar groups in close proximity is likely to be 'frustrated' (2) Hydration of HB donors appears to be weaker than that of HB ac
@MichaelKGilson I suspect 'stickiness' of Cl may be due to pull on π-cloud of aromatic ring ( https://t.co/ThBMTUlkhL) and that Cl is more polar than we think. Specific interactions with halogen more likely with Br linked to electron withdrawing carbon (e
@baoilleach Aromatic chloro substituents may be less lipophilic than we think: https://t.co/ThBMTUlkhL
Aromatic chlorine may be more polar than you think #MedChem #DrugDesign #HydrogenBond #SAR #logPalk #lipophilicity https://t.co/GeBo2Z9GiN
Partition coefficients are broadly relevant to #DrugDesign and #MolecularRecognition. Consideration of #HydrogenBond acidity/basicity may be useful/insightful in #logP prediction (re-post) #HBond #MedChem #PhysChem #cheminformatics #CompChem #MEP https:/
@DrBostrom @macinchem Becomes more manageable if you think in terms of representative sets of structurally prototypical representative acids/bases. There are spreadsheets of measured #pKa (63), #pKBHX (453) and alkane/water #logP (812) in ZIP file in suppl
@jchodera @neysanev @charleslbrooks @davidlmobley Likely challenge for continuum solvent models is when polar atoms are close together (solvation shells overlap) & logP for prototypical model compounds could be useful. This may be helpful https://t.co
@macinchem Analysis of alkane/water logP suggests that HB donors tend tend to be more readily desolvated than HB acceptors and this may be a factor to consider https://t.co/GeBo2Z9GiN
@curiouswavefn The Nantes group have measured HB basicity for aromatic rings and there is discussion of this and of polarity of aromatic rings in https://t.co/GeBo2Z9GiN
Influence of #HydrogenBonding on #logP (repost) #PhysChem #CompChem #DrugDesign #lipophilicity #QSPR #Nequimed #USP https://t.co/IlG1XRt5ev
@Protohedgehog @rickwahs @openscience @paleorxiv The zip file for this article gives SI example although code uses proprietary toolkit so not as open as I'd like https://t.co/yfHtqqCe1J
The influence of hydrogen bonding on partition coefficients (view-only; repost) #CompChem #PhysChem #cheminformatics https://t.co/IlG1XRt5ev
RT @pwk2013: @davidlmobley Amide carbonyl oxygen is arguably more polar than NH https://t.co/GeBo2Z9GiN
RT @pwk2013: @davidlmobley Amide carbonyl oxygen is arguably more polar than NH https://t.co/GeBo2Z9GiN
@davidlmobley Amide carbonyl oxygen is arguably more polar than NH https://t.co/GeBo2Z9GiN
The influence of hydrogen bonding on partition coefficients (view-only link) #CompChem #PhysChem #cheminformatics https://t.co/GeBo2Z9GiN
RT @pwk2013: The influence of #hydrogen #bonding on #partition #coefficients #logP #CompChem #PhysChem #cheminformatics #JCAMD https://t.…
The influence of #hydrogen #bonding on #partition #coefficients #logP #CompChem #PhysChem #cheminformatics #JCAMD https://t.co/1R1Yj3pvXD