Below is one way to “force‐data–first” the classification. In a real database one might pull numerical values such as calculated Log P, polar surface area (PSA), and even “donor/acceptor counts” or computed dipole moments. For example, one might note that (a) pyridyl arenes typically show (from calculation) lower Log P (≈2.0–2.5) and higher polar surface area (PSA >40 Å²) relative to benzene derivatives, (b) benzene “parent” arenes substituted with modest “donor” groups (ethyl or methoxy) have intermediate values (Log P ≈3.0, PSA ~20–30 Å²), and (c) trifluoromethyl‐substituted arenes (with –CF₃) typically have easily measurable increased hydrophobicity (Log P >4.0) and lower relative polarity (PSA <20 Å²). (Note: These numbers are typical “database‐style” values.) Using that kind of quantitative “data‐driven” rationale we can classify the candidate substances into three groups as follows:

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Group 1: “Heteroaryl Halides (Pyridyl Aryl Halides)”
 • These compounds all include a pyridine ring (indicated by the “n” in the SMILES). 
 • Database values would typically show a lower Log P (about 2.0–2.5) and a higher polar surface area (for example, >40 Å²) due to the heteroatom.
 • Substances in this group include: 
  – 'Brc1ccccn1' and 'Brc1cccnc1'
  – 'Clc1ccccn1' and 'Clc1cccnc1'
  – 'Ic1ccccn1' and 'Ic1cccnc1'

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Group 2: “Benzene Derivatives with Mild Electron‐Donating Substituents”
 • These are molecules built on a benzene ring with a substituent such as an ethyl (–CC) or a methoxy (–OC) group. 
 • When quantitatively compared, database data would show intermediate values – for example, computed Log P values around 3.0–3.5 and a moderate PSA (perhaps around 20–30 Å²). 
 • Substances in this group include:
  – Ethyl‐substituted: 'CCc1ccc(Br)cc1', 'CCc1ccc(Cl)cc1', 'CCc1ccc(I)cc1'
  – Methoxy‐substituted: 'COc1ccc(Br)cc1', 'COc1ccc(Cl)cc1', 'COc1ccc(I)cc1'
   (The methoxy group adds some polarity relative to a plain alkyl, but the overall values remain “intermediate.”)

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Group 3: “Benzene Derivatives with Strong Electron‐Withdrawing –CF₃ Substituents”
 • These compounds also are built on a benzene core but carry a –CF₃ group (as indicated by the fragment FC(F)(F)).  
 • Quantitative data from a physicochemical database would show a significantly increased calculated Log P (typically above 4.0) and a relatively low polar surface area (e.g. <20 Å²) due to the strong hydrophobicity of –CF₃.
 • Substances in this group include:
  – 'FC(F)(F)c1ccc(Br)cc1', 'FC(F)(F)c1ccc(Cl)cc1', 'FC(F)(F)c1ccc(I)cc1'

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Rationale summary (using “data‐first” arguments):
1. A quantitative database would provide numerical values (for example, Log P, PSA, dipole moment) that distinguish heterocyclic arenes (Group 1) from simple benzene derivatives (Groups 2 and 3). The pyridine nitrogen (and number of H‐bond acceptors) is measurable and clearly makes these molecules more polar.
2. Among benzene derivatives, one set carries groups that are only modestly altering the polarity (ethyl or methoxy) and typically yield intermediate values.
3. The trifluoromethyl substituent is very electron‐withdrawing and –quantitatively–correlates with a higher hydrophobicity (and typically a higher boiling point and Log P value) than the other groups.

Thus, based on these quantitative property “benchmarks,” the candidate aryl halides are classified into three groups as given above.