Organic Fluorine as a Hydrogen-Bond Acceptor: Recent Examples and Applications
Bibliographic record
Abstract
For more than three decades, the ability of a fluorine atom involved in a C–F bond to act as a hydrogen-bond acceptor has been a controversial issue. Throughout the years, more and more evidence has been published to support this hypothesis and it is now difficult to doubt the existence of the hydrogen bond with organic fluorine. However, since this interaction has low binding energies, it is sometimes difficult to clearly demonstrate its presence or effect in a system. In the present review, only the most recent examples from the literature are presented and the different techniques used to prove the presence of these C–F···H–X hydrogen bonds are compared and discussed according to the accepted criteria for hydrogen bonding detailed by a recent IUPAC committee. Even with its weak interaction energy, hydrogen bonds to organic fluorine have the potential to affect properties of practical systems in different spheres of chemistry. All the recent examples of such effects are highlighted. 1 Introduction 2 Properties 3 C(sp 2 )–F 3.1 O–H as Donor 3.2 N–H as Donor 3.3 C(sp 2 )–H as Donor 3.4 C(sp 3 )–H as Donor 4 C(sp 3 )–F 4.1 O–H as Donor 4.2 N–H as Donor 4.3 C(sp 2 )–H as Donor 4.4 C(sp 3 )–H as Donor 5 Conclusion
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How this classification was reachedexpand
Full frame machine prediction
Teacher imitationNot calibrated prevalence, not ground truth. Human validation pending. The Gemma side is a direct model label for every work in the frame, read from the title-only record. The Codex side is a classifier learned from the 10,348 direct Codex labels and calibrated to design-weighted sample rates; fields without enough sample support carry no Codex call. Candidate is the union of the two sides; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels.
Distilled classifier scores by category (both heads)
| Category | Codex | Gemma |
|---|---|---|
| Metaresearch | 0.000 | 0.000 |
| Meta-epidemiology (narrow) | 0.001 | 0.000 |
| Meta-epidemiology (broad) | 0.001 | 0.000 |
| Bibliometrics | 0.001 | 0.001 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.000 | 0.001 |
| Open science | 0.000 | 0.000 |
| Research integrity | 0.001 | 0.001 |
| Insufficient payload (model declined to judge) | 0.003 | 0.001 |
Machine scores (provisional)
The two teacher heads of the student model, read on this work. A score orders the frame for review; it never asserts a category, and the validation status ships verbatim with every row.
Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.
score_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from itClassification
machine, unvalidatedMachine predicted; a candidate call from one source (direct Gemma or distilled Codex), not a consensus.
How this classification was reached, model by model and score by score, is at the end of the page under "How this classification was reached".