reaction mass of N1,N3-bis(3-aminopropyl)-2-methyl-cyclohexane-1,3-diamine and N1,N3-bis(3-aminopropyl)-4-methyl-cyclohexane-1,3-diamine

Dissociation constant

Administrative data

Endpoint:

dissociation constant

Type of information:

(Q)SAR

Adequacy of study:

key study

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

results derived from a valid (Q)SAR model and falling into its applicability domain, with adequate and reliable documentation / justification

Justification for type of information:

1. SOFTWARE
SPARC On-Line Calculator (http://archemcalc.com/sparc-web/calc)

2. MODEL (incl. version number)
SPARC On-Line Calculator

3. SMILES OR OTHER IDENTIFIERS USED AS INPUT FOR THE MODEL
See section 'Test Material'.

4. SCIENTIFIC VALIDITY OF THE (Q)SAR MODEL
See attached QMRF.

5. APPLICABILITY DOMAIN
See attached QPRF.

6. ADEQUACY OF THE RESULT
- The model is scientifically valid (see attached QMRF).
- The model estimates the dissociation constant for ionization in water (pKa); information on the dissociation constant are required for substances manufactured or supplied in quantities of 100 t/y or more (see also attached QMRF).
- See attached QPRF for reliability assessment.

Data source

Reference

Reference 1

Reference Type:

other: SPARC calculation

Title:

Unnamed

Year:

2019

Report date:

2019

Reference 2

Reference Type:

publication

Title:

Estimation of Chemical Reactivity Parameters and Physical Properties of Organic Molecules Using SPARC (Book Chapter)

Author:

L. A. Carreira, S. Hilal and S. W. Karickhoff

Year:

1994

Bibliographic source:

Theoretical and Computational Chemistry, Quantitative Treatment of Solute/Solvent Interactions, Eds. P. Politzer and J. S. Murray, Elsevier Publishers

Reference 3

Reference Type:

publication

Title:

A Rigorous Test for SPARC's Chemical Reactivity Models: Estimation of more than 4300 Ionization pKa's

Author:

S. Hilal, S. W. Karickhoff and L. A. Carreira

Year:

1995

Bibliographic source:

Quant. Struc. Act. Rel., 14, 348

Reference 4

Reference Type:

grey literature

Title:

Unnamed

Year:

2003

Report date:

2003

Materials and methods

Principles of method if other than guideline:

Calculation of the macroscopic pKa using SPARC On-Line Calculator (http://archemcalc.com/sparc-web/calc)

GLP compliance:

no

Test material

Test material information

Constituent 1

Reference substance name:

N1,N3-bis(3-aminopropyl)-2-methyl-cyclohexane-1,3-diamine

Molecular formula:

C13H30N4

IUPAC Name:

N1,N3-bis(3-aminopropyl)-2-methyl-cyclohexane-1,3-diamine

Specific details on test material used for the study:

The calculation was performed for N1,N3-bis(3-aminopropyl)-2-methyl-cyclohexane-1,3-diamine (BI 858015), which is one of the representative compounds of the reaction mass of N1,N3-bis(3-aminopropyl)-2-methyl-cyclohexane-1,3-diamine and N1,N3-bis(3-aminopropyl)-4-methyl-cyclohexane-1,3-diamine (DAP-MCDA).

Results and discussion

Dissociating properties:

yes

Dissociation constant

Dissociation constant 1

No.:

#1

pKa:

5.82

Temp.:

25 °C

Remarks on result:

other: macroscopic pKa for transition from species 5 (max. fraction = 1.00) to species 6 (max. fraction = 0.86). Further details on the result can be found under "Any other information on results incl. tables"

Dissociation constant 2

No.:

#2

pKa:

8.04

Temp.:

25 °C

Remarks on result:

other: macroscopic pKa for transition from species 6 (max. fraction = 0.86) to species 7 (max. fraction = 0.47) and species 8 (max. fraction = 0.33). Further details on the result can be found under "Any other information on results incl. tables"

Dissociation constant 3

No.:

#3

pKa:

9.95

Temp.:

25 °C

Remarks on result:

other: macroscopic pKa for transition from species 7 (max. fraction = 0.47) and species 8 (max. fraction = 0.33) to species 2 (max. fraction = 0.29) and species 9 (max. fraction = 0.27).

Remarks:

Further details on the result can be found under "Any other information on results incl. tables"

Dissociation constant 4

No.:

#4

pKa:

10.76

Temp.:

25 °C

Remarks on result:

other: macroscopic pKa for transition from species 2 (max. fraction = 0.29) and species 9 (max. fraction = 0.27) to species 1 (max. fraction = 1.0). Further details on the result can be found under "Any other information on results incl. tables"

Any other information on results incl. tables

Table 1: SPARC has estimated 10 species for the present compound. Under environmental conditions (pH 4 to 9) the distribution of the single species is as follows:

Species	Fraction [%]: pH 4	Fraction [%]: pH 7	Fraction [%]: pH 9
#1	0	0	0.002
#2	0	0	0.047
#3	0	0.001	0.009
#4	0	0.009	0.001
#5	0.985	0.058	0
#6	0.015	0.861	0.088
#7	0	0.046	0.472
#8	0	0.033	0.334
#9	0	0	0.045
#10	0	0	0.003

(for details see attached QPRF)

Table 2: SMILES codes for the 10 species estimated by SPARC

Species	SMILES
#1	CC1C(NCCCN)CCCC1NCCCN
#2	NCCCNC1CCCC(NCCC[N+])C1(C)
#3	NCCCNC1CCCC([N+]CCC[N+])C1(C)
#4	NCCC[N+]C1CCCC([N+]CCC[N+])C1(C)
#5	CC1C(CCCC1([N+]CCC[N+]))[N+]CCC[N+]
#6	N(CCC[N+])C1CCCC([N+]CCC[N+])C1(C)
#7	NCCC[N+]C1CCCC(NCCC[N+])C1(C)
#8	N(CCC[N+])C1CCCC(NCCC[N+])C1(C)
#9	NCCCNC1CCCC([N+]CCCN)C1(C)
#10	NCCC[N+]C1CCCC([N+]CCCN)C1(C)