Boiling Point: Stein + Brown Method

The Stein + Brown boiling point method is a group contribution technique applicable to a broad range of organic chemicals. The technique is very easy to use - there is a single set of group contributions, no corrections for rings and no group interactions. A final "adjustment" calculation improves the boiling point estimates of higher molecular weight chemicals.

As with all group contribution techniques, the steps for generating an estimate are:

  1. dissect the chemical's structure into groups (see code lines 017 through 019)
  2. total the contributions for each group (see code lines 021 through 038)
  3. insert this contribution total into the model's equation (see code lines 040 and 041).

The final adjustment of the estimate is performed in code lines 043 through 048.


  1. S. E. Stein and R. L. Brown. "Estimation of Normal Boiling Points from Group Contributions." Journal of Chemical Information and Computer Science. Volume 34, number 3, page 581-587, 1994. (View on publisher's site)
Example Calculation

This example estimates the normal boiling point of 3-isopropyl-6-methylene-1-cyclohexene. (Note that the estimation technique distinguishes between acyclic groups and ring groups having the same molecular structure.)

Dissecting this molecular structure into the technique's groups gives the occurrences shown in the table to the right. Multiplying each group's occurrence by its contribution gives the subtotals shown in the table. Adding these subtotals together gives the total shown at the bottom of the table.

Inserting the total of the contributions into the model shown at the top of the page gives an estimate of 431.76K. This is in very good agreement with the reported experimental value of 447.15K.

Example Calculations
[*]=C-[*]2 (ss)128.1928.19
[*]=CH-[*] (ds)228.0356.06
[*]2-CH-[*] (ss)121.6621.66
[*]-CH2-[*] (ss)226.4452.88
Total - - - - - - 231.05
Example Results
Estimated Value445.75 K
Literature Value447.15 K
Evaluation Summary

The figure to the right shows that the estimation technique's errors are fairly consistent, i.e., errors do not depend upon the value of the estimated boiling point.

This evaluation was performed on January 30, 2023 using Cranium, Professional Edition version 5.0.

Summary Statistics
# Observations1429- - -
Avg Abs % Error3.7422%
Max Abs % Error115.79%
Min Abs % Error0.0174%
Avg Abs Error14.918K
Max Abs Error207.5K
Min Abs Error0.071706K
Avg Error-0.47781K
Max Error197.99K
Min Error-207.5K
Example Estimation Errors
ChemicalData [K]Estimates [K]% Error
Ethyl acetate350.30351.010.203
Ethyl thioacetate388.00411.746.119
Methyl salicylate493.65525.306.411
n-Decanoic acid543.15551.871.605
n-Heptanoic acid496.15499.970.770
Succinic acid591.00553.53-6.340
Accuracy Code

We continue to analyze estimation results to develop additional accuracy rules for Cranium and Synapse. The current rules are shown in the code to the right. (Note that the error value used in the rule was determined after several outliers were removed from the analysis.)

Online Calculation
This calculator demonstrates the use of the Stein + Brown boiling point estimation method. Begin by drawing a chemical's molecular structure in the editor below. (Press the editor's demo button to view a short video explaining its operation.)
Once you have draw the molecular structure, press the 'Estimate' button. The entered structure will be sent to the WebServer Edition of Cranium running on the internet. Cranium will dissect the chemical's structure into groups, total the contributions for each group, insert this total into the technique's model, and finally present the estimated value below.
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Estimated Boiling Point
- - -
Group Occurrences
Group Occurence
Group Structure
How It Works

The structure entered above is added to a property estimation request which is sent to an instance of our Cranium, Web Server Edition software product running on a Microsoft Azure virtual machine. Cranium processes the request - dissecting the structure into groups and estimating physical properties. These resulting values are then sent back to this webpage for display.

Click here to learn more about how you can use our Cranium Web Server to distribute your company's physical property data, estimates, and knowledge throughout your organization or contact us for further details.