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last update
29-Jan-2013

HSP Application note #43

Hydrogen Bonding Donor and Acceptor

2010.7.15

HSPiP Team Senior Developer, Dr. Hiroshi Yamamoto

 

We begin to start hydrogen bonding term(dH term) divided into donor and acceptor.

Hansen Solubility Parameters (HSP)

Hansen Solubility Parameters(HSP) were developed by Charles M. Hansen as a way of predicting if one material will dissolve in another and form a solution. They are based on the idea that "like dissolves like" where one molecule is defined as being 'like' another if it bonds to itself in a similar way.
Specifically, each molecule is given three Hansen parameters, each generally measured in MPa0.5:
dD:The energy from dispersion bonds between molecules
dP:The energy from dipolar intermolecular force between molecules
dH:The energy from hydrogen bonds between molecules.
These three parameters can be treated as Vector for a point in three dimensions also known as the Hansen space. The nearer two molecules HSP Vector are in this three dimensional space, the more likely they are to dissolve into each other.

What can perhaps be surprising is that one can assign HSP to so many different things. Gases like carbon dioxide, solids like carbon-60, sugar, and biological materials like human skin, depot fat, DNA, and even some proteins all have HSP. The list can be continued with drugs, polymers, plasticizers, and in fact any organic material and even many inorganic materials like salts. The only requirement for an experimental confirmation is that the material must behave differently in a sufficient number of test solvents upon contact.

Pirika JAVA Demo Applet calculate HSP. HSPLight is available here.
Please refer to e-Book of HSPiP if you want know more about HSP.
About the Power Tools that handle HSP more effectively.


We spend a lot of time to build new HSP distance and HSP similarity scheme.
But we need further study.

The first scheme, the total heat of vaporization should be identical.
dH2=dHdo2+dHac2  Scheme (1)
dHdo:donor term
dHac:acceptor term

And for the ratio of donor/acceptor, we apply Prof. Abraham, UCL (University College London) Abraham-D and Abraham-A.

dHdo:dHac=Abraham-D:Abraham-A Scheme (2)

So, we made the algorithm to determine dHdo, dHac that satisfy scheme(1) and(2).
And implement it into Y-MB.

We get dHdo, dHac for every compounds (thanks to prof. Abraham) but we just start research to find relationship solubility and dHdo, dHac.
The biggest problem is cross term.
Donor compounds will interact Acceptor very strongly.
So cross term decrease HSP distance. But how much this cross term decrease HSP distance.

HSP Distance

To calculate the distance (Ra) between Hansen parameters in Hansen space the following formula is used:

HSP distance(Ra)={4*(dD1-dD2)2 + (dP1-dP2)2 +(dH1-dH2)2 }0.5

 

Still we need researching.

 

We try to analyze the polymer for packing HSP with dHdo, dHac.
We apply SOM analysis and found that the strongly swelling solvents are divided into 2 groups.
But there is no significant difference from the point of dHdo, dHac.

Hcode name dD dP dH dHdo dHac Vol
6 acetic anhydride 16 11.7 10.2 0.00 10.20 95
7 acetone 15.5 10.4 7 0.12 7.00 73.8
11 acetophenone 18.8 10 4 0.10 4.00 117.4
17 acetylacetone 16.1 10 6.2 0.09 6.20 103.1
25 acrylonitrile 16 12.8 6.8 0.84 6.75 66.2
46 aniline 20.1 5.8 11.2 5.97 9.48 91.6
52 benzene 18.4 0 2 0.00 2.00 89.5
115 gamma-butyrolactone 18 16.6 7.4 0.10 7.40 76.5
122 carbon tetrachloride 17.8 0 0.6 0.60 0.00 97.1
156 chloroform 17.8 3.1 5.7 5.70 0.03 80.5
181 cyclohexane 16.8 0 0.2 0.00 0.20 108.9
182 cyclohexanol 17.4 4.1 13.5 7.17 11.44 105.7
195 trans-decahydronaphthalene 18 0 0 0.00 0.00 159.3
209 diacetone alcohol 15.8 8.2 10.8 3.00 10.37 124.3
254 diethyl carbonate 15.1 6.3 3.5 0.00 3.50 121.7
270 2-(2-methoxyethoxy)ethanol 16.2 7.8 12.6 3.27 12.17 118.2
285 N,N'-dimethylacetamide 16.8 11.5 10.2 0.31 10.20 93
297 N,N'-dimethylformamide 17.4 13.7 11.3 1.02 11.25 77.4
306 1,4-dioxane 17.5 1.8 9 0.00 9.00 85.7
325 ethyl alcohol 15.8 8.8 19.4 11.76 15.43 58.6
328 ethyl acetate 15.8 5.3 7.2 0.00 7.20 98.6
333 ethylbenzene 17.8 0.6 1.4 0.00 1.40 122.8
366 1,2-dibromoethane 19.2 3.5 6.6 2.83 5.96 86.6
385 ethylenediamine 16.6 8.8 17 0.54 16.99 67.3
396 formaldehyde 12.8 14.4 15.4 0.00 15.40 36.9
398 formic acid 14.6 10 22.12 19.86 9.76 37.9
404 furfural 18.6 14.9 7 0.02 7.00 83.2
417 hexane 14.9 0 0 0.00 0.00 131.4
429 isopentyl acetate 15.3 3.1 7 0.00 7.00 150.2
438 isophorone 17 8 5 0.00 5.00 150.3
456 methyl alcohol 14.7 12.3 22.3 13.97 17.38 40.6
464 methyl acetate 15.5 7.2 7.6 0.04 7.60 79.8
467 methyl acrylate 15.3 6.7 9.4 0.03 9.40 90.7
481 methyl ethyl ketone 16 9 5.1 0.06 5.10 90.2
491 4-methyl-2-pentanone 15.3 6.1 4.1 0.04 4.10 125.8
531 nitrobenzene 20 10.6 3.1 0.34 3.08 102.7
598 pyridine 19 8.8 5.9 0.06 5.90 80.9
617 tetrahydrofuran 16.8 5.7 5.7 0.09 5.70 81.9
637 toluene 18 1.4 2 0.02 2.00 106.6
649 trichloroethylene 18 3.1 5.3 4.75 2.36 90.1
659 triethyl phosphate 16.7 11.4 9.2 0.01 9.20 170.8
670 2,2,4-trimethylpentane iso-octane 14.1 0 0 0.00 0.00 165.5
698 o-xylene 17.8 1 3.1 0.00 3.10 121.1
814 p-chlorotoluene 19.1 6.2 2.6 0.03 2.60 119.1
997 2-methyltetrahydrofuran 16.9 5 4.3 0.11 4.30 100.2
1016 ethylacetoacetate 16.5 7.3 8.3 0.00 8.30 127.3
1037 methyl acetoacetate 16.4 8.6 8.9 0.02 8.90 108.3
1043 propionic anhydride 15.8 9 7.7 0.00 7.70 129.4
1145 dimethyl maleate 16.3 8.3 9.8 0.20 9.80 125.5

SOM: Self Organization Map Neural Network 

The 2D Map of "Smilar vector map to similar 2D position".

If we split dH to dHdo, dHac then HSP vector become 4 dimensions.
That is the very bad news for user. Because the Sphere and GUI can not expand to 4 dimensions.
So we start to develop SOM program to check vector similarity.

Pirika JAVA Demo Applet calculate SOM. SOMDemo is available here.

 

 

Study on solutions adsorption behavior of Pigments by measuring heat of wetting

This is Japanese paper written by painting company "Kansai-Paint".
They measure heat of sorption and heat of wetting for several pigments.
I showed the HSP of solvents and donor acceptor number for their study solvents.
In the original paper, they found correlation dH(hydrogen term) with heat of sorption and heat of wetting.
So, this time, I check the correlation dHdo, dHac with heat of sorption and heat of wetting.

dD dP dH Vol dHdo dHac
diethyl ether 15.49 2.9 4.6 104.7 0 4.6
cyclohexane 16.8 0 0.2 108.9 0 0.2
xylene 17.8 1 3.1 121.1 0 3.1
toluene 18 1.4 2 106.6 0 2
benzene 18.4 0 2 89.5 0.06 1.99
1,4-dioxane 17.5 1.8 9 85.7 0.12 8.99
aniline 20.1 5.8 11.2 91.6 5.15 9.95
butanol 16 5.7 15.8 92 9.63 12.52
propyl alcohol 16 6.8 17.4 75.1 10.3 14
ethyl alcohol 15.8 8.8 19.4 58.6 11.6 15.5
methyl alcohol 14.7 12.3 22.3 40.6 13.4 17.8
propylene glycol 16.8 10.4 21.3 73.7 12.2 17.5
ethylene glycol 17 11 26 55.9 16.2 20.3
Water 15.5 16 42.3 18 38.9 16.6

heat of sorption and heat of wetting for TiO2

The author's conclusion is that TiO2 is the Basic Pigment and interact Acidic Solvents.
dH donor and heat of sorption plot is almost same above.

Quinacridone A is believed to Acidic Pigment. So dH acceptor and heat of sorption plot, we can easily understand of this phenomena.

But heat of wetting is something very difficult to understand.

Solubility parameter and oral absorption
European Journal of Pharmaceutics and Biopharmaceutics 48 (1999) 259ー263
Luigi G. Martini*, Paul Avontuur, Ashley George1, Richard J. Willson, Patrick J. Crowley

namme % Oral absorption dD dP dH dHdo dHac
Metoprolol 102 17.59 5.93 9.55 9.30 2.16
Nordiazepam 99 21.33 11.24 1.06 1.02 0.26
Diazepam 97 20.46 8.35 1.46 1.44 0.26
Oxprenolol 97 17.44 6.56 10.86 10.78 1.30
Phenazone 97 18.92 6.67 8.06 8.05 0.21
Alprenolol 96 17.44 5.80 9.57 9.42 1.70
Practolol 95 18.24 9.89 12.81 11.57 5.49
Pindolol 92 18.82 7.57 10.73 9.28 5.40
Metolazone 64 20.81 12.09 9.15 8.89 2.16
Tranexamic acid 55 17.43 6.07 11.81 9.49 7.03
Atenolol 54 18.26 8.59 12.67 11.43 5.46
Sulpride 36 19.36 14.79 11.70 10.98 4.04
Mannitol 26 17.29 17.57 50.02 40.36 29.56
Foscarnet 17 20.65 30.71 47.21 43.49 18.38
Sulphasalazine 12 19.23 12.96 12.17 8.59 8.63
Olsalazine 2.3 17.77 9.52 17.03 8.18 14.94
Lactulose 0.6 18.99 16.61 42.53 35.26 23.78
Raffinose 0.3 18.66 16.34 39.34 32.94 21.50

In this case, Oral Absorption and dHac have very strong correlation.
Acid nature of stomach may play some role.

This study have just started.
And we ourselves did not understand completely.
So, we are not sure we add this dHdo, dHac number in ver. 3.1.X.
It will depend on user's feed back.

You can use dHdo, dHac in HSPiP V.3.1.X

HSPiP(Hansen Solubility Parameters in Practice)

The first edition of HSPiP that appeared in November, 2008, greatly enhanced the usefulness of the Hansen solubility parameters (HSP).

The HSP values of over 1200++ chemicals and 500 polymers are provided in convenient electronic format and have been revised and updated using the latest data sources in the second edition (March, 2009).

A third edition of the HSPiP appeared in March, 2010. There are now 10,000 compounds in the HSP file which also includes data on density, melting point, boiling point, critical parameters, Antoine constants and much more. The user is able to carry out many different sorts of optimisations of solubility, evaporation, diffusion, adhesion, create their own datasets (automatically if required) and explore the huge range of applications for HSP in coatings, paints, nanoparticles, cosmetics, pharma, organic photovoltaics and much more.

The 3rd Edition v3.1 was released on 12 December 2010. Current users can upgrade free (now v3.1.09) by downloading the latest .msi installer from http://hansen-solubility.com

The 4th Edition v4.0.x was released on 2 Jan. 2013. The Current users can upgrade with free charge.

2013.1.28 The Visual How to manual of HSPiP. You can understand what HSPiP can do.
Please check the Functional Group List whether your targets are available with HSPiP.
How to purchase HSPiP
2013..1.2 The HSPiP ver. 4 include Power Tools for HSPiP power user.

From HSPiP ver. 4, you can use 4D HSP more effectively. Please try Power Tool!

Search Solvents mixture.