reaction mass of 2,2,3,3,5,5,6,6-octafluoro-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)morpholine and 2,2,3,3,5,5,6,6-octafluoro-4-(heptafluoropropyl)morpholine

Additional physico-chemical information

Administrative data

Endpoint:

other: molecular bond strength and topology

Type of information:

calculation (if not (Q)SAR)

Remarks:

Migrated phrase: estimated by calculation

Adequacy of study:

key study

Study period:

8 Dec - 10 Dec 2015

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

other: Calculation by accepted quantum chemical software

Data source

Reference

Reference Type:

other company data

Title:

Unnamed

Year:

2015

Report date:

2015

Materials and methods

Test guideline

Qualifier:

no guideline available

Deviations:

not applicable

Principles of method if other than guideline:

Bond lengths and bond dissociation energy (BDE) using Spartan 14 software (trial version)

GLP compliance:

no

Test material

Test material information

Constituent 1

Reference substance name:

-

EC Number:

473-390-7

EC Name:

-

Cas Number:

1093615-61-2

Molecular formula:

C7F15NO

IUPAC Name:

2,2,3,3,5,5,6,6-octafluoro-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)morpholine; 2,2,3,3,5,5,6,6-octafluoro-4-(1,1,2,2,3,3,3-heptafluoropropyl)morpholine

Details on test material:

- Name of test material (as cited in study report): PF-NIPM (perfluoro-N-isopropylmorpholine), PF-NNPM (perfluoro-N-n-propylmorpholine)
- Smiles notation (if other than submission substance):
PF-NIPM: FC1(F)N(C(F)(F)C(F)(F)OC1(F)F)C(F)(C(F)(F)F)C(F)(F)F
PF-NNPM: FC1(F)N(C(F)(F)C(F)(F)OC1(F)F)C(F)(F)C(F)(F)C(F)(F)F

Results and discussion

Results:

The perfluorinated structures have higher bond energies and shorter carbon-nitrogen bond lengths than the corresponding hydrocarbons. As expected, carbon-fluorine bonds were longer than the analogous carbon-hydrogen bonds. A different molecular topology is expected due to fluorination.

Any other information on results incl. tables

Table 1. Modeled bond energy of the perfluoronated compounds and the corresponding hydrocarbons
Bond	Bond Energy (KJ/mol)
Structure	PF-NIPM	HC-NIPM	PF-NNPM	HC-NNPM
N-C	-740.0	-633.5	-819.3	-698.1
C-F or C-H	-500.1	-479.9	-462.4	-447.5
	Bond Energy (eV)
Structure	PF-NIPM	HC-NIPM	PF-NNPM	HC-NNPM
N-C	-7.7	-6.6	-8.5	-7.2
C-F or C-H	-5.2	-5.0	-4.8	-4.6

Table 2. Modeled bond length of the perfluorinated compounds and the corresponding hydrocarbons
Bond	Bond Length (Å)
Structure	PF-NIPM	HC-NIPM	PF-NNPM	HC-NNPM
N-C	1.4560	1.4723	1.4629	1.4804
C-F or C-H	1.3558	1.0961	1.3540	1.0980

Applicant's summary and conclusion

Conclusions:

Calculated bond energies were higher in the perfluorinated structures relative to hydrocarbon analogs, and C-N bonds were shorter. Overall molecular topology is expected to be different between hydrocarbon and fluorocarbon analogs.

Executive summary:

Molecular characteristics of two FC-770 isomers and the corresponding hydrocarbon analogs were modeled using Spartan 14 (trial version) software. The calculated bond energies were higher in the perfluorinated structures, and C-N bonds were shorter. Overall molecular topology is expected to be different between hydrocarbon and fluorocarbon analogs.

This study uses accepted, off-the-shelf molecular modeling software. It considered reliable with restrictions, and suitable for use in Risk Assessment and PBT analysis.