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HSP Application note #24

Functional Groups that can use in HSPiP


HSPiP Team Senior Developer, Dr. Hiroshi Yamamoto


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.
The 4th Edition v4.0.x was released on 2 Jan. 2013.
The v4.1.x was released on 18th Aug. 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.

How to purchase HSPiP
2013..1.2 The HSPiP ver. 4 include Power Tools for HSPiP power user.

Functional Group s (FG) used in version 3 (to ver. 4.1.x). Y-Predict use same FG.
Please check your compound whether all of functional groups are in the list.

Y-MB break molecule as to below list.
Y-MB choose larger FG if it available.
Y-MB can not handle charged atoms like N+, Cl-.

@ mark means Attach to.
# means triple bond.
The FG used in the cyclic part, _R is added.

Alkane groups

1 CH3 16 Bu 23 CH2CH2
2 CH2 17 2_Bu 24 CH2CH2_R
3 CH 18 iso_Bu 25 CH2CH2CH2
4 C 19 ter_Bu 110 CH2CH2CH2_R
11 CH2_R 20 Pr 128 CH2CH2CH2CH2
12 CH_R 21 iso_Pr 129 CH2CH2CH2CH2_R
13 C_R 22 Et 26 CH3_C_CH3

Olefine groups

5 CH2: 9 #CH
6 CH: 10 #C
7 C: 14 CH:_R
8 :C: 15 C:_R

Hydroxy groups

27 OH 117 OH@Ph
28 2_OH 121 OH@N
29 3_OH 147 OH_Other

Ketone groups

32 C:O 166 C:O_R@AR
33 C:O_R 120 C:O@Hal
165 C:O@AR 136 C:O@N

Ester groups

36 COO 161 COO@AR
37 COO_R 162 COO_R@AR
101 HCOO    

Carboxylic acid groups


Aldehyde groups

34 HCO 100 CHO@Ar

Nitrile groups

44 C#N 97 C#N@AR
Nitrile group is very difficult group. The properties are very depend on attached groups. We recommend only alkane or Aromatic attached nitrile.

Acid anhydride groups, Carbonate groups


Ether groups and other oxygen

30 O 130 O@P 106 O_reso
31 O_R 131 O@S 112 O-ethylene
102 O_R@AR 132 O@Si 151 O@Other
167 O@AR 104 OO 156 O_EPO
122 O@N     135 O:
Ether attached to halogen groups, especially CF2,
that loss ether properties.

Sulfer groups

46 SH 103 S@AR
47 S 105 S_R@AR
48 S_R 160 SH@AR
49 SS    

Other Sulfer groups

52 S:O 107 COS
119 S: 108 S_reso
    127 S{:O}2
SO2 group attach to NH2 or NH, the properties are similar to Amide.
But in ver. 3 we use just SO2+NH2.

Amine groups

38 NH2 87 NH2@Ar
39 NH 163 NH@AR
40 NH_R 164 NH_R@AR
41 N 139 N@AR
42 N_R 140 N_R@AR

Other nitrogen groups

153 N:C 144 N:_reso 50 N3res
154 N:C_R 157 N:CH 51 NHres
155 N:N 158 N:CH_R 43 N:
        148 N#C

Nitro groups

45 NO2 98 NO2@AR 134 NO3

Amide urethane groups

54 NHCO_R 56 NCO_R 152 C:ONHC:O

Aromatic groups

63 Ph 123 3s_Ph 141 1s_Naph 159 C:_rrr
65 o_Ph 124 4s_Ph 142 2s_Naph 145 CH:_reso
66 m_Ph 125 5s_Ph 143 3s_Naph 146 C:_reso
67 p_Ph 126 6s_Ph        

C:_reso means resonance carbon connect to alkane carbon.
CH:_reso means resonance carbon connect to hydrogen.
C:_rrr means resonance carbon like the naphthalene center 2 carbon.
Xs_Ph: means X substitute.

Hydrogen & Halogen Atom

88 H        
89 F 93 F@Ar 109 F_Ole
90 Cl 94 Cl@Ar 118 Cl_Ole
91 Br 95 Br@Ar  
92 I 96 I@Ar    

Halogen groups

70 CF3 74 CF2_R 81 CF
71 CCl3 75 CF2 84 CCl
72 CF2Cl 77 CCl2 114 CF_R
73 CFCl2 79 CFCl  
76 CHF2 82 CHF 68 C2F5
78 CHCl2 85 CHCl 69 C2F4H
80 CHFCl 111 CHCl_R  
83 CH2F 113 CHF_R  
86 CH2Cl 115 CFCl_R  
    116 CCl2_R    

Other hydrogen atom

61 H@N 62 H@C=O 138 H@Si

Other atom

137 Si 149 P 150 B
    133 P:O    

P is parameter missing for HSP

If I increase Functional Groups, properties estimation accuracy will increase.
But Functional Groups number increase, I need more and more data.

If you want to ask me to add new FG, please send me, at least, density, vapor pressure data, heat of vaporization, Refractive Index, Dipolemoment, dielectric constant for that molecule.

For Y-predict user. 2013.9.7

The Functional Group list is same with Y-MB.
There is one discussion about 3s_Ph or pyridazine compounds. For 3s_Ph, there are 1-2-3, 1-2-4, 1-2-5, 1-3-5 substitutions. But Y-MB and Y-Predict treat just same 3s_Ph. Some case, substitution position may change some properties, but to increase FG I need so many data but hard to get them.

For Y-Predict, I put the QEQ charge calculation function.

For these 3 compounds, FG list are same (N=_reso 2 , CH=_reso 4). But as you see, Nitrogen atom's charge are different (-0.045, -0.105, -0.064). So it means tree types of N=_reso exist. And in the calculation result, there is term of Symmetry Index. First and third molecule has 100% Symmetry, but second molecule is not 100% Symmetry. This Symmetry is "charged base" symmetry.The Max Plus Charge, Minimum Minus Charge are also different to these 3 molecules.

Application of these chrages and Symmetry to properties estimations scheme is just starting. If I find rational way to use of these Indexes, I will put them in new version.